Triethylamine → HCID 12791253, compound

HRID 1906159Notes

Reaction equation

HRID 1906159 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][C:11]([C:13]1[S:17][CH:16]=[N:15][C:14]=1[CH3:18])=[O:12].C(N(CC)CC)C.N1C=CC=NC1=O>ClCCl.CCO>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:10][C:11]([C:13]2[S:17][CH:16]=[N:15][C:14]=2[CH3:18])=[O:12])[CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 684012(1H)-PyrimidinoneHCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 185218775-Bromoacetyl-4-methylthiazole

Product 1

HCID 12791253HCID 12791253, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 5-chloropyrimidin-2-one (392 mg) and 5-bromoacetyl-4-methylthiazole (660 mg) in dry dichloromethane was treated with triethylamine (0.42 ml) and the resulting pale yellow solution was stirred at room temperature. After 1.25 h a precipitate had formed and the mixture was cooled in an ice-bath. The solid was collected, washed with cold dichloromethane and dried (346 mg). A second crop was obtained by concentration of the mother liquors (255 mg). The combined solids were recrystallised from acetone and then dichloromethane to give white crystals, the title pyrimidinone (186 mg) m.p. 212°-215° C. λmax (EtOH) 250.5 nm (E1cm1% 403), 266.5 nm (E1cm1% 401), 334 nm (E1cm1% 65). High performance liquid chromatography (reverse phase column, acetonitrilewater, 1:3) showed only one major component. N.M.R. (DMSO d6): 0.68 (2'-H), 1.28, 1.54 (two doublets, J 4 Hz) (4,6-H), 4.69 (--CH2 --), 7.21 τ (4' -CH3).

Workup

  1. customAfter 1.25 h a precipitate had formed
  2. temperaturethe mixture was cooled in an ice-bath
  3. customThe solid was collected
  4. washwashed with cold dichloromethane
  5. customdried (346 mg)
  6. customA second crop was obtained by concentration of the mother liquors (255 mg)
  7. customThe combined solids were recrystallised from acetone
  8. customdichloromethane to give white crystals

Sources & evidence

ORD record
ord-d14c061624d3404fbca2c0f5d421e358
Source dataset
uspto-grants-1987_03
Patent number
US04650800

Reaction notes

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