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

HRID 1052752Notes

Reaction equation

HRID 1052752 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.CC1(C)C(C)(C)OB([C:37]2[CH:38]=[N:39][CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=2)O1.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:37]1[CH:38]=[N:39][CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 533979043-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)pyridineHCID 118433733HCID 118433733, compound

Product 1

HCID 118433854(S)-2-(1-((6-Amino-5-(5-(trifluoromethyl)pyridin-3-yl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 39%

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 (83 mg, 0.19 mmol) was treated with 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)pyridine (130 mg, 0.47 mmol, prepared according to J. Aebi et al US 20090048238 19 Feb. 2009), sodium carbonate (2M, 350 μl, 0.70 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (15 mg, 0.02 mmol) according to the method described in Example 3 to give 37 mg (39% yield) of the title compound. Purity 99%.

Sources & evidence

ORD record
ord-60569d77cb7549aabc87593a7176a92a
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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