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

HRID 1052677Notes

Reaction equation

HRID 1052677 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]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1Br.[Cl:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[C:34]([OH:36])[CH:35]=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]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[C:32]1[CH:33]=[C:34]([OH:36])[CH:35]=[C:30]([Cl:29])[CH:31]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 53216311(3-Chloro-5-hydroxyphenyl)boronic acidHCID 118433733HCID 118433733, compound

Product 1

HCID 737762132-[(1S)-1-[[6-amino-5-(3-chloro-5-hydroxyphenyl)pyrimidin-4-yl]amino]ethyl]-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4-oneYield 32%

Procedure

(S)-2-(1-((6-Amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (100 mg, 0.23 mmol) was treated with (3-chloro-5-hydroxyphenyl)boronic acid (59 mg, 0.34 mmol), sodium carbonate (2M, 510 μl, 1.02 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (9 mg, 0.01 mmol) according to the method described in Example 3 to give 15 mg (32% yield) of the title compound as a solid. Purity 100%.

Sources & evidence

ORD record
ord-b68959ddd9e44e5880e03eaf5fd1cdee
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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