1-Bromopropane → N,N-Dipropyl-2,5-dimethyl-3-(2,4,6-trimethylphenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-amine

HRID 321978

Reaction equation

[CH2:1]([NH:4][C:5]1[C:6]2[C:7](=[C:12]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=3[CH3:24])[N:13]([CH3:15])[N:14]=2)[N:8]=[C:9]([CH3:11])[N:10]=1)[CH2:2][CH3:3].[OH-].[K+].Br[CH2:28][CH2:29][CH3:30]>CS(C)=O>[CH2:1]([N:4]([CH2:28][CH2:29][CH3:30])[C:5]1[C:6]2[C:7](=[C:12]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=3[CH3:24])[N:13]([CH3:15])[N:14]=2)[N:8]=[C:9]([CH3:11])[N:10]=1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of the product of step F (400 mg, 1.2 mmol), powder KOH (1.0 g) and 1-bromopropane (1 mL ) in 2 mL of DMSO was heated at 60° C. for 8 hours. The excess bromopropane was then evaporated. The mixture was partitioned between water and ether. The aqueous layer was separated and extracted with ether. The combined ether extracts were washed with water and brine, dried over Na2SO4 and concentrated to an oil. The oil was purified through silica gel column chromatography to give 260 mg of the title compound as an oil. 1H NMR (CDCl3): d 0.97 (t, 6 H), 1.76 (m, 4 H), 1.96 (s, 6 H), 2.32 (s, 3 H), 2.45 (s, 3 H), 3.77 (s, 3 H), 3.40-4.30 (br, 4 H), 6.95 (s, 2 H) ppm. The hydrochloride salt prepared in Ether/HCl melted at 210-13° C.

Workup

customThe excess bromopropane was then evaporated
customThe mixture was partitioned between water and ether
customThe aqueous layer was separated
extractionextracted with ether
washThe combined ether extracts were washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated to an oil
customThe oil was purified through silica gel column chromatography

Sources & evidence

ORD record: ord-97d00912150b4027907d2c7665e4dae2
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211187B1

Linked notes

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