Cyclopentyl Isocyanate → HCID 58138338, compound

HRID 1465904Notes

Reaction equation

HRID 1465904 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.[CH:14]1([N:19]=[C:20]=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15]1>C(Cl)Cl>[NH2:9][C:3]1[C:2]([F:1])=[CH:7][N:6]([C:20]([NH:19][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:21])[C:5](=[O:8])[N:4]=1

Participants

4

Reactant 2

HCID 643500Cyclopentyl IsocyanateHCID 178484257HCID 178484257, compound

Product 1

HCID 58138338HCID 58138338, compoundYield 5.6%

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 cyclopentyl isocyanate (0.168 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-N-cyclopentyl-5-fluoro-2-oxopyrimidine-1(2H)-carboxamide (0.018 g, 5%) as a white solid: mp 294-297° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.37 (d, J=6.59 Hz, 1H), 8.43 (s, 1H), 8.32 (d, J=7.58 Hz, 1H), 8.18 (s, 1H), 4.03 (sext, J=6.92 Hz, 1H), 1.94-1.85 (m, 2H), 1.68-1.39 (m, 6H); ESIMS m/z 239.1 ([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-ae4711ff12214c0e92ab226031087da2
Source dataset
uspto-grants-2015_04
Patent number
US09000002B2

Reaction notes

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