Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [NH:1]([C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])[C@H:2]([C:10]([NH:12][C@H:13]([C:23]([NH:25][C@H:26]([C:28]([NH:30][C@H:31]([C:36]([CH2:38][Cl:39])=[O:37])[CH2:32][CH:33]([CH3:35])[CH3:34])=[O:29])[CH3:27])=[O:24])[CH2:14][O:15]CC1C=CC=CC=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(OC)C=CC=CC=1>>[NH:1]([C:40]([O:42][CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)=[O:41])[C@H:2]([C:10]([NH:12][C@H:13]([C:23]([NH:25][C@H:26]([C:28]([NH:30][C@H:31]([C:36]([CH2:38][Cl:39])=[O:37])[CH2:32][CH:33]([CH3:35])[CH3:34])=[O:29])[CH3:27])=[O:24])[CH2:14][OH:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
Reactant: CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)[C@H](COCc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)CCl
Solvent: COc1ccccc1
Product: CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)CCl
Reaction time: 1.17 h

Procedure:
Z-Phe-Ser(Bzl)-Ala-LeuCH2Cl (0.71 g, 10.2 mmoles) was treated with a mixture of 15 mL of anhydrous HF and 1 mL of anisole in a commercial HF apparatus (Peptide Institute, Inc.). After 70 minutes at 0°, HF was removed by evaporation and the resulting residue was dried in vacuo over potassium hydroxide overnight. H-Phe-Ser-Ala-LeuCH2Cl.HF, 0.35 g, was obtained after triturating the residue with ether.
Reaction SMILES: C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[CH:29]=[C:28]([C:30]#[N:31])[N:27]([CH:32]5[CH2:36][CH2:35][CH2:34][CH2:33]5)[C:25]=4[N:26]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(OCC)C>[CH:32]1([N:27]2[C:25]3[N:26]=[C:21]([NH:20][C:17]4[CH:18]=[CH:19][C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[CH:15][N:16]=4)[N:22]=[CH:23][C:24]=3[CH:29]=[C:28]2[C:30]#[N:31])[CH2:36][CH2:35][CH2:34][CH2:33]1
Reactant: CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc4cc(C#N)n(C5CCCC5)c4n3)nc2)CC1
Solvent: CCOCC
Product: N#Cc1cc2cnc(Nc3ccc(N4CCNCC4)cn3)nc2n1C1CCCC1
Yield: 55.3 %

Procedure:
Using General Procedure A, 4-[6-(6-cyano-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (20 mg) gave crude product which is purified by SCX column (eluting with a 1:17 mixture of 2M NH3 in MeOH/dichloromethane) to give a solid. Trituration with diethyl ether gave 7-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitrile (8.8 mg, 7%) (over 2 steps). MS (ESI) m/z 389.2 (M+H)+ (method A).
Reaction SMILES: C(OC1C=CC(OC2C=CC(C(CC)(C)C)=CC=2)=C([N+]([O-])=O)C=1)C1C=CC=CC=1.C([O-])=O.[K+].[NH2:34][C:35]1[C:36]([O:42][C:43]2[CH:48]=[CH:47][C:46]([C:49]([CH2:52][CH3:53])([CH3:51])[CH3:50])=[CH:45][CH:44]=2)=[CH:37][CH:38]=[C:39]([OH:41])[CH:40]=1.[C:54]([C:59]1[CH:73]=[C:72]([C:74]([CH2:77][CH3:78])([CH3:76])[CH3:75])[CH:71]=[CH:70][C:60]=1[O:61][CH:62]([CH2:66][CH2:67][CH2:68][CH3:69])[C:63](Cl)=[O:64])([CH2:57][CH3:58])([CH3:56])[CH3:55]>O.C1(C)C=CC=CC=1.[Pd].C(O)(C)C>[C:54]([C:59]1[CH:73]=[C:72]([C:74]([CH2:77][CH3:78])([CH3:75])[CH3:76])[CH:71]=[CH:70][C:60]=1[O:61][CH:62]([CH2:66][CH2:67][CH2:68][CH3:69])[C:63]([NH:34][C:35]1[C:36]([O:42][C:43]2[CH:48]=[CH:47][C:46]([C:49]([CH2:52][CH3:53])([CH3:50])[CH3:51])=[CH:45][CH:44]=2)=[CH:37][CH:38]=[C:39]([OH:41])[CH:40]=1)=[O:64])([CH2:57][CH3:58])([CH3:55])[CH3:56]
Reactant: CCCCC(Oc1ccc(C(C)(C)CC)cc1C(C)(C)CC)C(=O)Cl
Reactant: CCC(C)(C)c1ccc(Oc2ccc(O)cc2N)cc1
Agent: [Pd]
Agent: CCC(C)(C)c1ccc(Oc2ccc(OCc3ccccc3)cc2[N+](=O)[O-])cc1
Agent: O=C[O-]
Solvent: Cc1ccccc1
Solvent: CC(C)O
Solvent: O
Product: CCCCC(Oc1ccc(C(C)(C)CC)cc1C(C)(C)CC)C(=O)Nc1cc(O)ccc1Oc1ccc(C(C)(C)CC)cc1
Temperature: 60 °C
Reaction time: 3 h
Yield: 91 %

Procedure:
In a 500-ml flask, place 19.6 g (0.05 m) of 5-benzyloxy-2-(4-t-pentyl-phenoxy)-nitrobenzene (3b), 80 ml of isopropyl alcohol and 40 ml of toluene. Heat the mixture to 60° C. Add 1.0 g of 5% Pd/C wet with 1 ml of water and 21.0 g (0.25 m) of potassium formate in 40 ml of water. Stir the reaction mixture vigorously at 60°-70° C. for 3 hrs under nitrogen. Cool the reaction mixture containing 5-amino-4-(4-t-pentylphenoxy)-phenol (4b; Y=4-t-pentylphenoxy) to 15° C. and add 20.3 g (0.05 m×1.05 @95%) of 2-(2,4-di-t-pentylphenoxy)-hexanoyl chloride (R′COZ; R′32 1-(2,4-di-t-pentylphenoxy)pentyl and Z=Cl) in 80 ml of toluene slowly in drop wise over 1 hr period. Stir the mixture at 15° C. for another 30 min. Filter off catalyst and wash with a small volume of toluene and water. Separate toluene solution, wash with 100 ml of 1N HCl twice, and concentrate under a reduced pressure to a thick oil. Add 200 ml of heptane to the oil with gentle stirring. Cool in an ice-water bath for 1 hr. Collect solid, wash with heptane, and dry in a vacuum oven to give 27.4 g (91%) of 5-{2-(2,4-di-t-pentylphenoxy)hexanoyl}amino-4-(4-t-pentylphenoxy)-phenol (5b; Y=4-t-pentylphenoxy and R′=1-(2,4-di-t-pentylphenoxy)pentyl).