Potassium Carbonate → HCID 118434019, compound

HRID 1052768Notes

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]=1[C:28]1[CH:29]=[N:30][CH:31]=[C:32]([OH:34])[CH:33]=1.[F:35][C:36]([F:40])([F:39])[CH2:37]I.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[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:18]=[CH:19][CH:20]=[CH:21][CH:22]=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:28]1[CH:29]=[N:30][CH:31]=[C:32]([O:34][CH2:37][C:36]([F:40])([F:39])[F:35])[CH:33]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (S)-2-(1-((6-amino-5-(5-hydroxypyridin-3-yl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (49 mg, 0.11 mmol), 1,1,1-trifluoro-2-iodoethane (13 μl, 0.13 mmol) and potassium carbonate (30 mg, 0.22 mmol) in N,N-dimethylformamide (3 ml) was stirred at 120° C. under microwave irradiation for 2 h. Further 1,1,1-trifluoro-2-iodoethane (13 μl, 0.13 mmol) and potassium carbonate (15 mg, 0.11 mmol) were added and the reaction mixture was stirred at 120° C. under microwave irradiation for 2 h. The residue was purified by reverse phase using SP1® Purification System to give 32 mg (55% yield) as a solid. Purity 100%.

Workup

stirringthe reaction mixture was stirred at 120° C. under microwave irradiation for 2 h
customThe residue was purified by reverse phase
custom® Purification System
customto give 32 mg (55% yield) as a solid

Sources & evidence

ORD record: ord-6e12e94de01a4819865743b59de591e2
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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