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

HRID 1052673Notes

Reaction equation

HRID 1052673 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.[F:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[C:34]([F:37])[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]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[C:32]1[CH:31]=[C:30]([F:29])[C:35]([OH:36])=[C:34]([F:37])[CH:33]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 52911287(3,5-Difluoro-4-hydroxyphenyl)boronic acidHCID 118433733HCID 118433733, compound

Product 1

HCID 73776932(S)-2-(1-((6-Amino-5-(3,5-difluoro-4-hydroxyphenyl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 15.2%

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 (260 mg, 0.59 mmol) was treated with (3,5-difluoro-4-hydroxyphenyl)boronic acid (154 mg, 0.89 mmol), sodium carbonate (2 M, 1.33 mL, 2.66 mmol) and 2′-(dimethylamino)-2-biphenylyl-palladium(II) chloride dinorbornylphosphine complex (17 mg, 0.03 mmol) according to the method described in the Preparation 17. The residue was purified using SP1® Purification System (0% to 60%, hexane-ethyl acetate) to give 44 mg (15% yield) of the title compound as a white solid. Purity 95%.

Workup

  1. customdescribed in the Preparation 17
  2. customThe residue was purified
  3. customSP1® Purification System (0% to 60%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-6cfb8d18c76040fdb7786aa3c5af3d76
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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