Ethyl Acetate → HCID 13913229, compound

HRID 579744Notes

Reaction equation

Cl[C:2]1[C:3]2[CH2:10][CH2:9][CH:8]([O:11][CH3:12])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.[OH-].[Na+].C(OCC)(=O)C>C(O)C>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([NH:13][C:2]2[C:3]3[CH2:10][CH2:9][CH:8]([O:11][CH3:12])[C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:15][CH:16]=1)#[N:19]

Participants

Conditions

Temperature: 130 °C

Procedure

0.92 g of 4-chloro-6,7-dihydro-7-methoxy-5H-cyclopenta[d]pyrimidine [prepared as described in step (e) above] and 0.59 g of p-aminobenzonitrile were dissolved in 5 ml of ethanol, and the solution was stirred at 130° C. for 10 minutes. At the end of this time, the mixture was cooled to room temperature, and the resulting solid reaction product was pulverized. 50 ml of a 1N aqueous solution of sodium hydroxide and 200 ml of ethyl acetate were added to the resulting powder, and the ethyl acetate layer was separated, washed with water and dried over anhydrous sodium sulfate. The ethyl acetate was evaporated off under reduced pressure, and the resulting residue was purified by silica gel column chromatography, eluted with ethyl acetate, to give 0.54 g of the title compound as colorless crystals melting at 167°-169° C.

Workup

temperatureAt the end of this time, the mixture was cooled to room temperature
customthe resulting solid reaction product
customthe ethyl acetate layer was separated
washwashed with water
dry with materialdried over anhydrous sodium sulfate
customThe ethyl acetate was evaporated off under reduced pressure
customthe resulting residue was purified by silica gel column chromatography
washeluted with ethyl acetate

Sources & evidence

ORD record: ord-89eea037dfc74eab92106e66db29f01f
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04749704

Reaction notes

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