Propyl isocyanate → 4-(dimethylamino-methyleneamino)-5-fluoro-2-oxo-2H-pyrimidine-1-carboxylic acid propylamide

HRID 1038948Notes

Reaction equation

HRID 1038948 reaction equation
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH2:14]([N:17]=[C:18]=[O:19])[CH2:15][CH3:16]>ClCCl>[CH2:14]([NH:17][C:18]([N:6]1[CH:7]=[C:2]([F:1])[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]1=[O:8])=[O:19])[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 61033Propyl isocyanateHCID 178484257HCID 178484257, compound

Product 1

HCID 508983554-(dimethylamino-methyleneamino)-5-fluoro-2-oxo-2H-pyrimidine-1-carboxylic acid propylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 7 milliliter (mL) screw-cap vial were added dichloromethane (CH2Cl2; 5 milliliters (mL)), N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (200 milligrams (mg), 1.09 millimoles (mmol)), and propyl isocyanate (94 mg, 1.10 mmol). The mixture was shaken at room temperature for 16 hours (h). After evaporation and recrystallization of the crude product from CH2Cl2 and heptane, the title compound was isolated as a white solid (274 mg, 94%): mp 266-268° C.; 1H NMR (300 MHz, CDCl3) δ10.42 (br s, 1H), 8.84 (s, 1H), 8.46 (d, J=6.6 Hz, 1H), 3.39-3.30 (m, 2H), 3.25 (s, 6H), 1.70-1.57 (m, 2H), 0.97 (t, J=7.4 Hz, 3H); ESIMS m/z 270 ([M+H]+).

Workup

  1. customTo a 7 milliliter (mL) screw-cap vial
  2. customAfter evaporation and recrystallization of the crude product from CH2Cl2 and heptane

Sources & evidence

ORD record
ord-9af78ea029b84d3397f87e23a488e18d
Source dataset
uspto-grants-2013_10
Patent number
US08552020B2

Reaction notes

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