6-Methoxy-2-methylpyrimidin-4-amine → (7-Methoxy-5-methylimidazo[2,1-f]pyrimidin-2-yl)-phenylmethanone

HRID 236289Notes

Reaction equation

HRID 236289 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH2:10])[CH:4]=1.Br[CH2:12][C:13](=O)[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15]>O1CCCC1.CCOCC>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[N:6]2[CH:12]=[C:13]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])[N:10]=[C:5]2[CH:4]=1

Participants

5

Reactant 2

HCID 5494356-Methoxy-2-methylpyrimidin-4-amineHCID 125689113-Bromo-1-phenylpropane-1,2-dione

Product 1

HCID 13478385(7-Methoxy-5-methylimidazo[2,1-f]pyrimidin-2-yl)-phenylmethanoneYield 66.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2.1 g of 6-methoxy-2-methyl-4-pyrimidinamine in dry tetrahydrofuran was treated with a solution of 5.4 g of 3-bromo-1-phenyl-1,2-propanedione in 5 ml of dry ether. After stirring overnight, the mixture was chilled and the precipitated salt filtered off. A suspension of the salt in dry ethanol was refluxed for 1.5 hours, chilled, and filtered. The solid was shaken with a mixture of chloroform and aqueous sodium bicarbonate and the organic layer was evaporated to dryness under reduced pressure. The residue was chromatographed in ethyl acetate on silica to obtain 2.7 g of (7-methoxy-5-methyl-imidazo[1,2-c]pyrimidin-2-yl)-phenylmethanone as a yellow crystalline solid melting at 165°-7° C.

Workup

  1. temperaturethe mixture was chilled
  2. filtrationthe precipitated salt filtered off
  3. additionA suspension of the salt in dry ethanol
  4. temperaturewas refluxed for 1.5 hours
  5. temperaturechilled
  6. filtrationfiltered
  7. stirringThe solid was shaken with a mixture of chloroform and aqueous sodium bicarbonate
  8. customthe organic layer was evaporated to dryness under reduced pressure
  9. customThe residue was chromatographed in ethyl acetate on silica

Sources & evidence

ORD record
ord-1a4a3f0f49234fa5b11d092a5cc62dcc
Source dataset
uspto-grants-1987_02
Patent number
US04643999

Reaction notes

Loading…