Reaction SMILES: Cl[C:2]1[N:3]=[C:4]([NH:11][CH:12]2[CH2:14][CH2:13]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:15][C:16]1[CH:28]=[CH:27][C:19]2[O:20][C:21]([CH3:26])([CH3:25])[C:22](=[O:24])[NH:23][C:18]=2[CH:17]=1.C([O-])([O-])=O.[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(O)(C)C>[CH:12]1([NH:11][C:4]2[C:5]3[O:10][CH:9]=[CH:8][C:6]=3[N:7]=[C:2]([NH:15][C:16]3[CH:28]=[CH:27][C:19]4[O:20][C:21]([CH3:25])([CH3:26])[C:22](=[O:24])[NH:23][C:18]=4[CH:17]=3)[N:3]=2)[CH2:14][CH2:13]1
Reactant: CC1(C)Oc2ccc(N)cc2NC1=O
Reactant: Clc1nc(NC2CC2)c2occc2n1
Agent: [Pd]
Agent: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1
Agent: O=C(/C=C/c1ccccc1)/C=C/c1ccccc1
Solvent: ClCCl
Solvent: CC(C)(C)O
Product: CC1(C)Oc2ccc(Nc3nc(NC4CC4)c4occc4n3)cc2NC1=O
Temperature: 85 °C
Reaction time: 8 h
Yield: 36.7 %

Procedure:
To a flask was added 2-chloro-N-cyclopropylfuro[3,2-d]pyrimidin-4-amine (7.82 g, 37.3 mmol), 6-amino-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (8.60 g, 44.7 mmol, Example #3, Step C), K2CO3 (6.18 g, 44.7 mmol) and t-BuOH (249 mL). To the mixture was added Pd2dba3 (2.05 g, 2.24 mmol) and X-Phos (2.13 g, 4.47 mmol). The flask was de-gassed and vented with N2 three times. The mixture was heated to about 85° C. and stirred overnight. The mixture was diluted with EtOAc (700 mL) and washed with water (700 mL). The aqueous layer was extracted with EtOAc (2×300 mL). The combined organic layers were dried with MgSO4, filtered through a pad of Celite® and concentrated in vacuo. The material was purified by column chromatography (300 g silica gel) using a gradient of 30 to 100% EtOAc/DCM. The material was suspended in 30% EtOAc/DCM (150 mL) and heated to about 77° C. with stirring. MeOH (20 mL) was added gradually to the hot solution until a clear solution resulted. The mixture was allowed to stir for about 1 h and then cooled to rt. The precipitate formed was collected by filtration to give a solid. The mother liquor was kept in the refrigerator overnight and the resulting precipitate was collected by filtration to yield a second batch of the product. The two solids were combined. The material was then suspended in DCM and filtered. The precipitate was dried in a vacuum oven at about 70° C. for about 18 h. The material was then pulverized using a mortar and pestle and dried in the vacuum oven at about 80° C. for about 16 h. The material was taken up in IPA (200 mL) and the suspension was heated to about 50° C. with stirring for about 2 h. The mixture was brought to rt and filtered. The precipitate was dried in a vacuum oven at about 80° C. for about 16 h. The material was dissolved in MeOH (200 mL) and evaporated under reduced pressure. The residue was dried in a vacuum oven at about 80° C. for about 16 h. The material was suspended in water (200 mL) and sonicated for about 10 min then stirred vigorously for about 1 h. The mixture was filtered and the precipitate was dried in a vacuum oven at about 80° C. for about 20 h to provide 6-(4-(cyclopropylamino)furo[3,2-d]pyrimidin-2-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (5.0 g, 37%): LC/MS (Table 2, Method c) Rt=1.87 min.; MS m/z: 366 (M+H)+. Syk IC50=A