Potassium Carbonate → HCID 178480074, compound

HRID 1930586Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:10]=[C:11]([OH:26])[C:12]3[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16][CH2:15][C:13]=3[N:14]=2)=[CH:4][CH:3]=1.[CH3:27][N:28]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[N:29]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(O)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Cl-].[Cl-].[Fe+2].[Pd+2]>[OH:26][C:11]1[C:12]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16][CH2:15][C:13]=2[N:14]=[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([C:31]3[CH:30]=[N:29][N:28]([CH3:27])[CH:32]=3)=[CH:3][CH:4]=2)[N:10]=1

Participants

Conditions

Temperature: 110 °C

Procedure

tert-Butyl 2-(4-bromophenylamino)-4-hydroxy-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (1.4 g, 3.32 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H pyrazole (0.691 g, 3.32 mmol), dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium (II), Pd-118 (0.108 g, 0.17 mmol) and potassium carbonate (1.837 g, 13.29 mmol) in DMF (5 mL), water (2.5 mL) and ethanol (0.833 mL) were charged in a thick wall glass, which was sealed and heated at 110° C. for 20 minutes. The raction mixture was allowed to cool down, the crude was filtered through celite and the filtercake washed with ethanol. The solvent was evaporated under reduced pressure. The crude was used in the next step without further purification. MS (ESI) (M+1) m/z 423

Workup

customwas sealed
temperatureto cool down
filtrationthe crude was filtered through celite
washthe filtercake washed with ethanol
customThe solvent was evaporated under reduced pressure
customThe crude was used in the next step without further purification

Sources & evidence

ORD record: ord-475ac817a732471586a262ced4452c7c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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