Sodium hydride → HCID 15702771, compound

HRID 2050519Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.[H-].[Na+].[C:23](N1C=CN=C1)(N1C=CN=C1)=[S:24]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 5.0 g of 7-(4-chlorophenyl)-4,5-dihydro-6-methylpyrazolo(1,5-a)pyrimidine-3-carboxamide (Example 35) 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 for 0.5 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 4.2 g of the desired product as cream colored crystals, mp. 283-285° C.

Workup

stirringThis mixture is stirred for 0.5 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-bc3fa485d82a45148c64a949cc85db6c
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05013737

Reaction notes

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