Sodium hydride → HCID 54465927, compound

HRID 2050520Notes

Reaction equation

[Cl: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][C:9]=2[CH3:20])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[C:23](N1C=CN=C1)(N1C=CN=C1)=[S:24]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[C:12]4[N:11]([C:23](=[S:24])[NH:19][C:17](=[O:18])[C:16]=4[CH:15]=[N:14]3)[CH2:10][C:9]=2[CH3:20])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 5.0 g of 7-(3-chlorophenyl)-4,5-dihydro-6-methylpyrazolo(1,5-a)pyrimidine-3-carboxamide (Example 36) and 0.2 liters of dry tetrahydrofuran is stirred and cooled to -78° C. in a dry ice-acetone bath, then 1.43 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 3.19 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 0.5 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 4.0 g of the desired product as cream colored crystals, mp 289-291° C.

Workup

stirringThis mixture is stirred at -78° C. for 1.5 hours
stirringstirring
temperatureto warm to room temperature
stirringis stirred for 48 hours
customthe reaction is quenched with 0.5 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-63977939c56a43a3b61797c7a776cc69
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05013737

Reaction notes

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