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

HRID 1052342Notes

Reaction equation

HRID 1052342 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]([Br:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1I.[F:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:35]=1[OH:36].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]([Br:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[C:32]1[CH:33]=[CH:34][C:35]([OH:36])=[C:30]([F:29])[CH:31]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 23005361(3-Fluoro-4-hydroxyphenyl)boronic acidHCID 118433900(S)-2-(1-((6-Amino-5-iodopyrimidin-4-yl)amino)ethyl)-5-bromo-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 118433808(S)-2-(1-((6-Amino-5-(3-fluoro-4-hydroxyphenyl)pyrimidin-4-yl)amino)ethyl)-5-bromo-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 0.2%

Procedure

(S)-2-(1-((6-Amino-5-iodopyrimidin-4-yl)amino)ethyl)-5-bromo-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (90 mg, 0.16 mol) was treated with (3-fluoro-4-hydroxyphenyl)boronic acid (38 mg, 0.24 mol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (22 mg, 0.02 mol) and a solution of sodium carbonate (2M, 317 μl, 0.73 mol) according to the method described in Example 3 to give 150 mg of the title compound that was used in the next step without any further purification.

Sources & evidence

ORD record
ord-cacc378f59e8435f89af14e732693e78
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…