2-Bromo-4'-methylacetophenone → HCID 12795539, compound

HRID 980169Notes

Reaction equation

HRID 980169 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH2:19]Br)=[O:18])=[CH:13][CH:12]=1>C(N(CC)CC)C.C(O)C>[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[N:7]([CH2:19][C:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:10])=[CH:12][CH:13]=2)=[O:18])[CH:8]=1

Participants

5

Reactant 2

HCID 692722-Bromo-4'-methylacetophenoneHCID 126485235-Chloropyrimidin-2-ol hydrochloride

Product 1

HCID 12795539HCID 12795539, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 5-chloropyrimidin-2-one hydrochloride (501 mg) and 2-bromo-4-methylacetophenone (638 mg) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for one and three quarter hours, then cooled and the solid filtered off. The filtrate was evaporated, the residue was diluted with water (100 ml) and the product was extracted with ethyl acetate (3×50 ml). This was combined with the solid and crystallised from acetone: yield 306 mg, m.p. 214°-217° dec: λmaxEtOH 253 nm (ε 19760), 332 nm (ε 2620), λinf 232 nm (ε 11040).

Workup

  1. temperaturecooled
  2. filtrationthe solid filtered off
  3. customThe filtrate was evaporated
  4. additionthe residue was diluted with water (100 ml)
  5. extractionthe product was extracted with ethyl acetate (3×50 ml)
  6. customcrystallised from acetone

Sources & evidence

ORD record
ord-3c7aed6350e446838ea75c2111055eeb
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

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