Triethylamine → HCID 58138291, compound

HRID 1260415

Reaction equation

HRID 1260415 reaction equation
[F:1][C:2]1[C:3]([NH:9][C:10](=[O:12])[CH3:11])=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH3:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1.CCN(CC)CC>C(Cl)Cl>[F:1][C:2]1[C:3]([NH:9][C:10](=[O:12])[CH3:11])=[N:4][C:5](=[O:8])[N:6]([C:18](=[O:19])[C:17]2[CH:21]=[CH:22][C:14]([CH3:13])=[CH:15][CH:16]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 178474477HCID 178474477, compound

Product 1

HCID 58138291HCID 58138291, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a round-bottomed flask containing N-(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide (350 mg, 2.04 mmol) in CH2Cl2 (20 mL) was added 4-methylbenzoyl chloride (316 mg, 2.2 mmol) and Et3N (454 mg, 4.5 mmol) at 0° C. The mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with CH2Cl2 (30 mL), washed with saturated aqueous sodium chloride (satd aq NaCl) solution (1×15 mL), dried over Na2SO4 and concentrated in vacuo. The crude solid was purified by reverse phase chromatography to yield N-(5-fluoro-1-(4-methylbenzoyl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide as a white solid (16 mg, 3%): mp 146.9-148.2° C.; 1H NMR (acetone-d6) δ 9.75 (s, 1H), 8.64 (d, J=2.5 Hz, 1H), 8.06 (d, J=8.2 Hz, 2H), 7.44 (d, J=8.1 Hz, 2H), 2.47 (s, 3H), 2.32 (s, 3H).

Workup

  1. washwashed with saturated aqueous sodium chloride (satd aq NaCl) solution (1×15 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude solid was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-9a0a6522bb3c4cb594922a07ba17dea0
Source dataset
uspto-grants-2013_06
Patent number
US08470839B2

Linked notes

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