Pentane, 1-isocyanato- → HCID 58138333, compound

HRID 1465903Notes

Reaction equation

HRID 1465903 reaction equation
[F:1][C:2]1[C:3]([N:9]=CN(C)C)=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH2:14]([N:19]=[C:20]=[O:21])[CH2:15][CH2:16][CH2:17][CH3:18]>C(Cl)Cl>[NH2:9][C:3]1[C:2]([F:1])=[CH:7][N:6]([C:20]([NH:19][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:21])[C:5](=[O:8])[N:4]=1

Participants

4

Reactant 2

HCID 206036Pentane, 1-isocyanato-HCID 178484257HCID 178484257, compound

Product 1

HCID 58138333HCID 58138333, compoundYield 6.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (0.25 g, 1.35 mmol) in CH2Cl2 (5 mL) was added pentyl isocyanate (0.194 mL, 1.49 mmol) forming a solution that was stirred at room temperature for 3 h. The solvent was removed to give a solid residue that was purified by reverse phase chromatography (gradient, CH3CN/H2O) to yield 4-amino-5-fluoro-2-oxo-N-pentylpyrimidine-1(2H)-carboxamide (0.022 g, 6%) as a white solid: mp 289-292° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.27 (t, J=5.49 Hz, 1H), 8.43 (s, 1H), 8.32 (d, J=7.58 Hz, 1H), 8.19 (s, 1H), 3.24 (q, J=6.99 Hz, 2H), 1.51-1.46 (m, 2H), 1.3-1.21 (m, 4H), 0.85 (t, J=6.59 Hz, 3H); ESIMS m/z 241.2 ([M−H]−).

Workup

  1. customforming a solution that
  2. customThe solvent was removed
  3. customto give a solid residue that
  4. customwas purified by reverse phase chromatography (gradient, CH3CN/H2O)

Sources & evidence

ORD record
ord-abaa6bf75a054c909de04fe5a2dccdb8
Source dataset
uspto-grants-2015_04
Patent number
US09000002B2

Reaction notes

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