Water → 1-(4-Triphenylmethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)methylamine

HRID 349557Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:14]2[CH2:19][CH2:18][CH2:17][N:16]3[N:20]=[CH:21][C:22]([C:23]#[N:24])=[C:15]23)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F-].[K+].O>O1CCCC1>[C:31]1([C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:14]2[CH2:19][CH2:18][CH2:17][N:16]3[N:20]=[CH:21][C:22]([CH2:23][NH2:24])=[C:15]23)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a suspension of lithium aluminum hydride (2.7 g) in tetrahydrofuran (150 ml) was added 4-triphenylmethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (8.5 g) under ice-cooling. The mixture was stirred at 65° C. for 16 hours. After cooling on an ice bath, potassium fluoride (16.5 g) and water (5 ml) were added to the reaction mixture. The insoluble materials were removed by filtration. The filtrate was concentrated in vacuo to give 1-(4-triphenylmethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)methylamine (8.4 g) as a solid.

Workup

temperaturecooling
temperatureAfter cooling on an ice bath
customThe insoluble materials were removed by filtration
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-e80b60d728e64fb0a0526fd838302315
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179801B2

Reaction notes

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