Ethyl isocyanate → HCID 58138345, compound

HRID 1465910Notes

Reaction equation

HRID 1465910 reaction equation
[F:1][C:2]1[C:3]([NH:9][C:10](=[O:12])[CH3:11])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14]>C1COCC1>[C:10]([NH:9][C:3]1[C:2]([F:1])=[CH:7][N:6]([C:16]([NH:15][CH2:13][CH3:14])=[O:17])[C:5](=[O:8])[N:4]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 178474475HCID 178474475, compound

Product 1

HCID 58138345HCID 58138345, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-(5-fluoro-2-hydroxypyrimidin-4-yl)acetamide (as prepared in U.S. Pat. No. 3,309,359; 0.25 g, 1.46 mmol) in dry THF (5 mL) was added ethyl isocyanate (0.127 mL, 1.61 mmol), and the mixture was stirred at room temperature for 1 h. The solvent was removed in vacuo, and the solid residue was suspended in Et2O (10 mL). The suspension was suction filtered and washed with Et2O (2×10 mL). The resulting solid was dried in vacuo to yield 4-acetamido-N-ethyl-5-fluoro-2-oxopyrimidine-1(2H)-carboxamide (0.350 g, 99%) as a white solid: mp 233-235° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.89 (s, 1H), 10.01 (s, 1H), 8.62 (d, J=7.0 Hz, 1H), 3.40-3.27 (m, 2H), 2.30 (s, 3H), 1.15 (t, J=7.2 Hz, 3H); ESIMS m/z 241

Workup

  1. customas prepared in U.S
  2. customThe solvent was removed in vacuo
  3. filtrationfiltered
  4. washwashed with Et2O (2×10 mL)
  5. customThe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-fe39f368f78446ac83ff51714ec479a4
Source dataset
uspto-grants-2015_04
Patent number
US09000002B2

Reaction notes

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