Vertellus → 4-Pyrimidinebutanol,2-amino-6-[[3-fluoro-4-(1h-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino]-
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH2:10][C:11](OCC)=[O:12])[CH:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]4[NH:30][CH:31]=[CH:32][C:25]=34)=[C:19]([F:33])[CH:18]=2)[N:3]=1.[B-].[Na+]>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]4[NH:30][CH:31]=[CH:32][C:25]=34)=[C:19]([F:33])[CH:18]=2)[N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
300 mg (0.67 mmol) of 4-(2-amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}pyrimidin-4-yl)butan-1-ol (from example 132) are suspended in 15 ml of ethanol, and 253 mg (6.66 mmol) of sodium borohydrate are added a little at a time at RT. The mixture is stirred at RT for 24 hours and then concentrated, and ethyl acetate and water are added. The organic phase is dried over sodium sulfate. The product is purified by column chromatography (silica gel 60; gradient column, mobile phase: DCM:methanol=9:1 to 3:1). 133 mg (27%) of the starting material are recovered. The product fraction is re-purified by preparative HPLC. This gives the title compound.