Sodium hydride → HCID 15702769, compound

HRID 2073192Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[N:14]=[CH:15][C:16]([C:17]([NH2:19])=[O:18])=[C:12]3[NH:11][CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[C:22](N1C=CN=C1)(N1C=CN=C1)=[S:23]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[C:12]4[N:11]([C:22](=[S:23])[NH:19][C:17](=[O:18])[C:16]=4[CH:15]=[N:14]3)[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 63.0 g of 7-(3-fluorophenyl)-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide (Example 6) and 2.5 liters of dry tetrahydrofuran was stirred and cooled to -78° C. in a dry-ice-acetone bath, then 18.0 g of sodium hydride (60% dispersion in mineral oil) was added in one portion. This mixture was stirred at -78° C. for 11/2 hours then 40.0 g of 1,1'-thiocarbonyldiimidazole was added and stirring was continued at -78° C. for 2 hours. The mixture was allowed to warm to room temperature and was stirred for 48 hours, and then the reaction was quenched with 2.5 liters of water, neutralized with 5% aqueous hydrochloric acid. The crystalline solid that formed was collected, washed with ether and dried to give 54.6 g of the desired product as cream-colored crystals, m.p. 298°-300° C.

Workup

stirringThis mixture was stirred at -78° C. for 11/2 hours
stirringstirring
temperatureto warm to room temperature
stirringwas stirred for 48 hours
customthe reaction was quenched with 2.5 liters of water
customThe crystalline solid that formed
customwas collected
washwashed with ether
customdried

Sources & evidence

ORD record: ord-ec60830dc21644e6a1b9925d9a527e7c
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04916137

Reaction notes

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