Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH:14](Br)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH:14]([N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([OH:1])[CH2:3]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
Reactant: BrC(c1ccccc1)c1ccccc1
Reactant: OC1CCCNC1
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: O
Solvent: CN(C)C=O
Product: OC1CCCN(C(c2ccccc2)c2ccccc2)C1
Yield: 78.8 %

Procedure:
5.05 g (0.05 mole) of 3-hydroxypiperidine and 13.82 g (0.1 mole) of potassium carbonate were suspended in 100 ml of dimethylformamide. 12.36 g (0.05 mole) of benzhydryl bromide were then added to the mixture, whilst stirring, and the mixture was stirred for 10 hours at room temperature. At the end of this time, the mixture was poured into 700 ml of water and extracted with ethyl acetate. The extracts were washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was subjected to silica gel column chromatography, and 10.53 g (yield 78%) of the title compound were obtained as a colorless material from the fractions eluted with a 9:1 by volume mixture of toluene and ethyl acetate.
Reaction SMILES: [C:1]([CH2:9][C:10]#[N:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.CO[C:18](OC)([N:20]([CH3:22])[CH3:21])[CH3:19]>C1C=CC=CC=1>[C:1](/[C:9](=[C:18](/[N:20]([CH3:22])[CH3:21])\[CH3:19])/[C:10]#[N:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
Reactant: N#CCC(=O)c1ccccc1
Reactant: COC(C)(OC)N(C)C
Solvent: ClC(Cl)Cl
Solvent: c1ccccc1
Product: C/C(=C(/C#N)C(=O)c1ccccc1)N(C)C

Procedure:
To a solution of 14.5 g. (0.10 m) of benzoylacetonitrile in 100 ml. of chloroform, cooled in an ice-salt bath, was added 13.3 g. (0.1 m) of N,N-dimethylacetamide dimethylacetal in 20 ml. chloroform. The reaction mixture was stirred in the ice-salt bath for 2 hours, then evaporated in vacuo to an orange oil. The oil was dissolved in 150 ml. benzene and passed through Magnesol®. The filtrate was evaporated and the oil thus obtained was dissolved in 50 ml. benzene to which pet ether was added until the solution became cloudy. The precipitate which formed upon cooling was collected. The solid was recrystallized twice from benzene-pet ether, with charcoal treatment to yield 5.8 g. (27%) of light yellow crystals, m.p. 105°-106° C.
Reaction SMILES: [Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[CH:3]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=N1.CN1CCOCC1.N1CC=CC1>CN(C)C=O>[N:19]1([C:6]([C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=2[CH3:11])=[O:8])[CH2:20][CH:25]=[CH:24][CH2:23]1
Reactant: CN(C)C(On1nnc2ccccc21)=[N+](C)C
Reactant: Cc1cc(Br)ccc1C(=O)O
Agent: C1=CCNC1
Agent: F[B-](F)(F)F
Solvent: CN1CCOCC1
Solvent: CN(C)C=O
Product: Cc1cc(Br)ccc1C(=O)N1CC=CC1
Temperature: 25 °C
Reaction time: 16 h

Procedure:
25.0 g (0.12 mol) of 4-bromo-2-methylbenzoic acid is dissolved in 250 mL of dimethylformamide and after the addition of 41.7 g (0.13 mol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU), 14.3 mL (0.13 mol) of N-methylmorpholine and 9.6 mL (0.12 mol) of 2,5-dihydropyrrole, the mixture is stirred for 16 hours at ambient temperature. Then it is poured onto ice water and extracted with ethyl acetate. The combined organic extracts are washed with sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated by evaporation. Yield: 31.6 g (97% of theory); Rf value: 0.45 (silica gel; dichloromethane/ethanol=19:1).
Reaction SMILES: [Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:11][O:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.[CH3:23][NH2:24]>>[Cl:1][C:2]1[N:3]=[C:4]([NH:24][CH3:23])[C:5]2[CH2:11][O:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1
Reactant: CN
Reactant: FC(F)(F)c1ccc(C2COCc3c(Cl)nc(Cl)nc32)cc1
Product: CNc1nc(Cl)nc2c1COCC2c1ccc(C(F)(F)F)cc1

Procedure:
2,4-dichloro-8-(4-(trifluoromethyl)phenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine (Preparation Z) was reacted as described in Preparation Xa with methanamine to give 2-chloro-N-methyl-8-(4-(trifluoromethyl)phenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine (Preparation Zb). LC-MS (M+H)+=344.1.
Reaction SMILES: Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:3]=1.[CH:17]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18]1.CCN(C(C)C)C(C)C>Cl.CCCCO>[CH:17]1([NH:22][C:2]2[CH:3]=[C:4]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[N:5]=[CH:6][N:7]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1
Reactant: NC1CCCC1
Reactant: COc1ccc(Nc2cc(Cl)ncn2)cc1
Agent: Cl
Solvent: CCN(C(C)C)C(C)C
Solvent: CCCCO
Product: COc1ccc(Nc2cc(NC3CCCC3)ncn2)cc1
Temperature: 200 °C
Yield: 83 %

Procedure:
75 mg of 6-chloro-N-(4-methoxyphenyl)pyrimidine-4-amine in the form of a hydrochloride, 26 mg of cyclopentylamine and 90 mg of DIPEA were dissolved in 1 mL of n-BuOH and charged into a microwave vial and the vial obtained was heated to 200° C. for 45 minutes under microwave irradiation. The reaction was monitored by TLC. The crude product was obtained by evaporating n-BuOH. Purification was carried out by column chromatography using EtOAc. N4-Cyclopentyl-N6-(4-methoxyphenyl)pyrimidine-4,6-diamine in the form of a colorless solid was obtained.