1-(3-Bromo-4-fluorophenyl)-1-(2-tetrahydropyrimidinyl)methanol → 2-(3-Bromo-4-fluorobenzoyl)-2,3,4,5-tetrahydropyrimidine

HRID 272660Notes

Reaction equation

HRID 272660 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:11]2[NH:16][CH2:15][CH:14]=[CH:13][NH:12]2)[OH:10])[CH:5]=[CH:6][C:7]=1[F:8]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[C:9]([CH:11]1[NH:16][CH2:15][CH2:14][CH:13]=[N:12]1)=[O:10]

Participants

4

Reactant 1

HCID 688999571-(3-Bromo-4-fluorophenyl)-1-(2-tetrahydropyrimidinyl)methanol

Product 1

HCID 574239842-(3-Bromo-4-fluorobenzoyl)-2,3,4,5-tetrahydropyrimidineYield 81%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(3-bromo-4-fluorophenyl)-1-(2-tetrahydropyrimidinyl)methanol (23.4 g, 81.5 mmol) and manganese dioxide (70.8 g, 815 mmol) in methylene chloride is stirred at room temperature for 3 days and filtered through diatomaceous earth. The filtercake is washed with chloroform. The filtrates are combined and concentrated to dryness to afford the title compound as a yellow-green solid, 18.9 g (81% yield), identified by NMR and mass spectral analyses. 1H NMR (500 MHz, CDCl3) δ 8.51 (m, 1H), 8.23 (m, 1H), 7.15 (t, J=8.4 Hz, 1H), 6.10 (br s, 1H), 3.65 (br s, 2H), 3.41 (br s, 2H), 1.83 (m, 2H); ESI MS m/z 284 [C11H10BrFN2O+H]+.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. washThe filtercake is washed with chloroform
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-469fc7e682ed4a16b2f642de5a4aab74
Source dataset
uspto-grants-2008_11
Patent number
US07456186B2

Reaction notes

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