Acetic Anhydride → 4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl acetate
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N+:5]([O-])=[C:4]2[CH2:9][CH2:10][CH2:11][C:3]=12.[C:12]([O:15]C(=O)C)(=[O:14])[CH3:13]>>[C:12]([O:15][CH:9]1[C:4]2[N:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]=2[CH2:11][CH2:10]1)(=[O:14])[CH3:13]Participants
Conditions
- Temperature
- 110 °C
Procedure
A solution of 40 g of 4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrmidine-1-oxide [prepared as described in step (a) above] in 1 liter of acetic anhydride was added dropwise, whilst heating at 50° C., to 1.5 liters of acetic anhydride. After the addition was complete, the solution was stirred at 110° C. for 2 hours. At the end of this time, the mixture was cooled to room temperature, and the solvent was evaporated off under reduced pressure. 400 ml of a mixture of toluene and hexane were added to the resulting residue, the mixture was stirred, and the solvent was separated by decantation; these operations were repeated a further 2 times. The decanted solvents were combined and then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography, using chloroform as the eluent, to give 39.3 g of the title compound as a colorless oil.
Workup
- additionAfter the addition
- temperatureAt the end of this time, the mixture was cooled to room temperature
- customthe solvent was evaporated off under reduced pressure
- addition400 ml of a mixture of toluene and hexane were added to the resulting residue
- stirringthe mixture was stirred
- customthe solvent was separated by decantation
- customevaporated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-17be821fba7d412e8f67b60166c242a2
- Source dataset
- uspto-grants-1988_06
- Patent number
- US04749704
Reaction notes
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