Dimethylformamide → [2-Amino-6-(1-methyl-piperidin-4-ylamino)-pyridin-3-yl]-(5-fluoro-2-methoxy-phenyl)-methanone

HRID 30131Notes

Reaction equation

F[C:2](F)(F)C(O)=O.[NH2:8][C:9]1[C:14]([C:15]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])=[O:16])=[CH:13]N=[C:11]([NH:26][CH:27]2[CH2:32]CNC[CH2:28]2)[N:10]=1.C(=O)([O-])[O-].[K+].[K+].IC.[CH3:41][N:42]([CH3:45])[CH:43]=O>C(OCC)(=O)C>[NH2:8][C:9]1[C:14]([C:15]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])=[O:16])=[CH:13][CH:2]=[C:11]([NH:26][CH:27]2[CH2:28][CH2:43][N:42]([CH3:45])[CH2:41][CH2:32]2)[N:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [4-amino-2-(piperidin-4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone trifluoroacetic acid salt (0.0575 mmol, Example 22) in N,N-dimethylformamide (1.5 mL) were added potassium carbonate (55.6 mg, 0.4024 mmol, Aldrich) and iodomethane (14.8 mg, 0.104 mmol, Aldrich 99.5%) in N,N-dimethylformamide (0.35 mL). The reaction was stirred at 0° C. for 4 hrs. The resulting mixture was diluted with ethyl acetate (30 mL), washed with water, brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified on reversed phase HPLC to give [2-Amino-6-(1-methyl-piperidin-4-ylamino)-pyridin-3-yl]-(5-fluoro-2-methoxy-phenyl)-methanone as a white solid (4.8 mg, 24% yield). HRMS, observed: 358.1810, Calcd for M+: 358.1805.

Workup

washwashed with water, brine
dry with materialdried over sodium sulfate
customevaporated in vacuo
customThe residue was purified on reversed phase HPLC

Sources & evidence

ORD record: ord-a5fd57a524414ea9b654591ec4def49b
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423051B2

Reaction notes

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