Methylamine → HCID 178518757, compound

HRID 1727299Notes

Reaction equation

HRID 1727299 reaction equation
C([N:9]1[C:14](=[O:15])[C:13]([F:16])=[CH:12][N:11]([C@H:17]2[CH2:20][C@@H:19]([CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18]2)[C:10]1=[O:30])(=O)C1C=CC=CC=1.CN>C(O)C>[F:16][C:13]1[C:14](=[O:15])[NH:9][C:10](=[O:30])[N:11]([C@H:17]2[CH2:20][C@@H:19]([CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18]2)[CH:12]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 178519534HCID 178519534, compound

Product 1

HCID 178518757HCID 178518757, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3-benzoyl-5-fluoro-1-[cis-3-(benzyloxymethyl)cyclobutyl]uracil (1.5 g) in ethanol (100 mL) was treated with 2 M methylamine in ethanol (5 mL) and aged for 2 h at ambient temperature. Solvent was removed under vacuum and the resulting residue was purified by chromatography over silica gel with a gradient from 50% to 60% ethyl acetate in hexanes to give 5-fluoro-1-[cis-3-(benzyloxymethyl)cyclobutyl]uracil (250 mg, 25% for two steps) as a white solid. 1H NMR (CDCl3, 400 MHz): δ 2.19 (m, 2H), 2.36 (s, 1H), 2.50 (m, 2H), 3.47 (d, J=3.84 Hz, 2H), 4.56 (s, 2H), 4.94 (m, 1H), 7.33 (m, 5H), 7.64 (d, J=6.2 Hz, 1H), 9.57 (broad s, 1H); 13C NMR (CDCl3, 125 MHz)): δ 27.91, 31.17, 46.53, 71.88, 73.60, 125.45, 125.88, 127.92, 128.12, 128.788, 138.26, 139.16, 142.32, 149.68, 157.26.

Workup

  1. customSolvent was removed under vacuum
  2. customthe resulting residue was purified by chromatography over silica gel with a gradient from 50% to 60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-872337005ba94015aa0c1d518bc9e9ac
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

Loading…