Water → HCID 10341896, compound

HRID 1435241Notes

Reaction equation

HRID 1435241 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4]([NH:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[N:3]=1.Br[CH2:27][O:28][C:29](=[O:31])[CH3:30].O>CN(C)C=O>[CH3:27][O:28][C:29](=[O:31])[CH2:30][N:23]1[CH2:22][CH2:21][CH:20]([NH:19][C:4]2[N:3]=[C:2]([NH2:1])[C:7]([C:8](=[O:9])[C:10]3[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=3[O:17][CH3:18])=[CH:6][N:5]=2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 962WaterHCID 68536Bromomethyl acetateHCID 9997668[4-Amino-2-(piperidin-4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone

Product 1

HCID 10341896HCID 10341896, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [4-amino-2-(piperidin-4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone (60 mg, 0.17 mmol, Example 59) and bromomethylacetate (60 mg, 0.39 mmol, Aldrich) in dimethylformamide (1.5 mL) was stirred at room temperature for 6 hours. The solution was poured into water and extracted into methylene chloride (2×). The combined organic extracts were washed with 5% aqueous sodium bicarbonate. The organic solution was dried (Na2SO4) and solvent was removed under vacuum to give a crude solid. Purification was by silica gel chromatography to give [4-[4-amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidin- 1-yl]-acetic acid methyl ester as a white solid. HRMS, observed: 418.1888; Calcd for M+: 418.1885.

Workup

  1. extractionextracted into methylene chloride (2×)
  2. washThe combined organic extracts were washed with 5% aqueous sodium bicarbonate
  3. dry with materialThe organic solution was dried (Na2SO4) and solvent
  4. customwas removed under vacuum
  5. customto give a crude solid
  6. customPurification

Sources & evidence

ORD record
ord-c37daecc05be40368ada76eeab201307
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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