Triethylamine → HCID 58138311, compound

HRID 1880204Notes

Reaction equation

HRID 1880204 reaction equation
[CH2:1]([N:8]([CH3:17])[C:9]1[C:14]([F:15])=[CH:13][NH:12][C:11](=[O:16])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24](Cl)=[O:25].CCN(CC)CC>C(Cl)Cl>[CH2:1]([N:8]([CH3:17])[C:9]1[C:14]([F:15])=[CH:13][N:12]([C:24]([O:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18])=[O:25])[C:11](=[O:16])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69489Pentyl chloroformateHCID 178482714HCID 178482714, compound

Product 1

HCID 58138311HCID 58138311, compoundYield 6.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(benzyl(methyl)amino)-5-fluoropyrimidin-2(1H)-one (0.200 g, 0.858 mmol) in CH2Cl2 (18 mL) were added N-pentyl chloroformate (0.142 g, 0.944 mmol) and Et3N (0.263 mL, 1.88 mmol) at 0° C. The mixture was allowed to warm to room temperature and stirred an additional 3 h. The crude reaction mixture was evaporated to dryness and the residue was triturated with methyl t-butyl ether (MTBE; 4×5 mL) to remove triethylamine hydrochloride. The combined organic layers were evaporated in vacuo. The crude product was purified by reverse phase chromatography. Pentyl 4-(benzyl(methyl)amino)-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (20.1 mg, 6.7%) was isolated as a yellow gum: 1H NMR (methanol-d4) δ 8.04 (d, J=6.2 Hz, 1H), 7.38-7.25 (m, 5H), 4.24 (t, J=6.6 Hz, 2H), 3.21 (d, J=3.3 Hz, 2H), 1.78-1.65 (m, 3H), 1.37 (dd, J=9.2, 5.5 Hz, 6H), 0.92 (t, J=7.1 Hz, 3H); ESIMS m/z 348 ([M+H]+).

Workup

  1. customThe crude reaction mixture
  2. customwas evaporated to dryness
  3. customthe residue was triturated with methyl t-butyl ether (MTBE; 4×5 mL)
  4. customto remove triethylamine hydrochloride
  5. customThe combined organic layers were evaporated in vacuo
  6. customThe crude product was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-7aaa79fa665840bbbcba0ee007339fbb
Source dataset
uspto-grants-2012_11
Patent number
US08318758B2

Reaction notes

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