Trityl chloride → 4-Triphenylmethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 349556Notes

Reaction equation

[N:1]1[N:5]2[CH2:6][CH2:7][CH2:8][NH:9][C:4]2=[C:3]([C:10]#[N:11])[CH:2]=1.[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[C:12]1([C:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:9]2[CH2:8][CH2:7][CH2:6][N:5]3[N:1]=[CH:2][C:3]([C:10]#[N:11])=[C:4]23)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (6.9 g) in pyridine (70 ml) was added triphenylmethyl chloride (15.6 g), and the mixture was stirred at 65° C. for 4 hours. After evaporation of the solvent in vacuo, the residue was dissolved in chloroform, and the solution was washed with 10% aqueous citric acid solution. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with diisopropyl ether and dried in vacuo to give 4-triphenylmethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (16.2 g) as a solid.

Workup

customAfter evaporation of the solvent in vacuo
dissolutionthe residue was dissolved in chloroform
washthe solution was washed with 10% aqueous citric acid solution
customThe organic layer was separated
extractionthe aqueous layer was extracted with chloroform
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was triturated with diisopropyl ether
customdried in vacuo

Sources & evidence

ORD record: ord-6a10c7c4fb37495f81bb1dcd20c1d68d
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179801B2

Reaction notes

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