Bromotrimethylsilane → HCID 178485575, compound

HRID 2279887Notes

Reaction equation

HRID 2279887 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[C:5]([NH:12][C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]3[CH:34]=[CH:33][C:27]([CH2:28][CH2:29][PH:30](=[O:32])[O-:31])=[CH:26][C:25]=3[O:35][CH3:36])[N:14]=2)=[CH:4][CH:3]=1.Br[Si](C)(C)C>N1C=CC=CC=1>[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[C:5]([NH:12][C:13]2[C:18]([C:19]([F:22])([F:20])[F:21])=[CH:17][N:16]=[C:15]([NH:23][C:24]3[CH:34]=[CH:33][C:27]([CH2:28][CH2:29][PH:30](=[O:31])[OH:32])=[CH:26][C:25]=3[O:35][CH3:36])[N:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 178485574HCID 178485574, compound2×

Product 1

HCID 178485575HCID 178485575, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)methylphosphinate (Compound 61C, 130 mg, 0.215 mmol) in pyridine (10 mL) was charged with bromotrimethylsilane (0.171 mL, 1.29 mmol). The reaction mixture stirred at rt for 16 hrs. The reaction was concentrated in vacuo to solid to afford 100 mg of the title compound (79%). 1H NMR (400 MHz, CD3OD) δ 9.04 (br. s., 1H), 8.36 (s, 1H), 7.72 (br. s., 1H), 7.56 (d, J=8.8 Hz, 1H), 7.05 (s, 1H), 6.84-6.95 (m, 1H), 3.86 (s, 3H), 3.20 (d, J=17.7 Hz, 2H), 2.94 (s, 3H), 1.42 (s, 3H). MS (ESI): m/z=589.38/591.37 [M+H]+. UPLC: tR=1.19 min (UPLC-TOF: polar—2 min).

Workup

  1. concentrationThe reaction was concentrated in vacuo to solid

Sources & evidence

ORD record
ord-942d2e2da3364bb4a0b3f689a91fff3a
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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