Sodium Carbonate → (S)-2-(1-((6-Amino-5-(3-fluoro-5-hydroxyphenyl)pyrimidin-4-yl)amino)ethyl)-3-phenyl-5-(phenylthio)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052680Notes

Reaction equation

HRID 1052680 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([S:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1Br.[F:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[C:40]([OH:42])[CH:41]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([S:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[C:38]1[CH:39]=[C:40]([OH:42])[CH:41]=[C:36]([F:35])[CH:37]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 447173083-Fluoro-5-hydroxybenzeneboronic acidHCID 118433835HCID 118433835, compound

Product 1

HCID 73776788(S)-2-(1-((6-Amino-5-(3-fluoro-5-hydroxyphenyl)pyrimidin-4-yl)amino)ethyl)-3-phenyl-5-(phenylthio)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 3%

Procedure

(S)-2-(1-((6-Amino-5-bromopyrimidin-4-yl)amino)ethyl)-3-phenyl-5-(phenylthio)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (230 mg, 0.29 mmol) was treated with (3-fluoro-5-hydroxyphenyl)boronic acid (68 mg, 0.44 mmol), sodium carbonate (2M, 660 μl, 1.32 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (36 mg, 0.04 mmol) according to the method described in Example 3 to give 4 mg (3% yield) of the title compound as a solid. Purity 91%.

Sources & evidence

ORD record
ord-35feead8178f44f6afa2411448483a99
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…