Sodium hydride → HCID 15702769, compound

HRID 2050518Notes

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 11) and 2.5 liters of dry tetrahydrofuran is stirred and cooled to -78° C. in a dry ice-acetone bath, then 18.0 g of sodium hydride (60 percent dispersion in mineral oil) is added in one portion This mixture is stirred at -78° C. for 1.5 hours then 40.0 g of 1,1'-thiocarbonyldiimidazole is added and stirring is continued at -78° C. for 2 hours. The mixture is allowed to warm to room temperature and is stirred for 48 hours and then the reaction is quenched with 2.5 liters of water and neutralized with 5 percent aqueous hydrochloric acid. The crystalline solid that forms is collected, washed with ether and dried to give 54.6 g of the desired product as cream colored crystals, mp 298-300° C.

Workup

stirringis stirred at -78° C. for 1.5 hours
stirringstirring
temperatureto warm to room temperature
stirringis stirred for 48 hours
customthe reaction is quenched with 2.5 liters of water and neutralized with 5 percent aqueous hydrochloric acid
customThe crystalline solid that forms is collected
washwashed with ether
customdried

Sources & evidence

ORD record: ord-c97a39a128274d1eaa96cd14c098b1b2
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05013737

Reaction notes

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