Sodium Carbonate → HCID 73776787, compound

HRID 1052674Notes

Reaction equation

HRID 1052674 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.[OH:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[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]([C:36]([F:39])([F:37])[F:38])[CH:35]=[C:30]([OH:29])[CH:31]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 45790688[3-Hydroxy-5-(trifluoromethyl)phenyl]boronic acidHCID 118433733HCID 118433733, compound

Product 1

HCID 73776787HCID 73776787, compoundYield 25%

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-hydroxy-5-(trifluoromethyl)phenyl)boronic acid (70 mg, 0.34 mmol), sodium carbonate (108 mg, 1.02 mmol) and 2′-(dimethylamino)-2-biphenylyl-palladium(II) chloride dinorbornylphosphine complex (6 mg, 0.01 mmol) according to the method described in the Preparation 17. The residue was purified by reverse phase using SP1® Purification System to give 30 mg (25% yield) of the title compound as a solid. Purity 98%.

Workup

  1. customdescribed in the Preparation 17
  2. customThe residue was purified by reverse phase
  3. custom® Purification System

Sources & evidence

ORD record
ord-48c79c4816854b7e8c23f0e351ea8033
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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