Trimethylsilylacetylene → 7-Difluoromethyl-5-(3-ethoxy-phenyl)-3-trimethylsilanylethynyl-pyrazolo[1,5-a]pyrimidine

HRID 2237891Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][N:5]2[C:10]([CH:11]([F:13])[F:12])=[CH:9][C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH3:22])[CH:15]=3)=[N:7][C:6]=12.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25]>>[F:12][CH:11]([F:13])[C:10]1[N:5]2[N:4]=[CH:3][C:2]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])=[C:6]2[N:7]=[C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH3:22])[CH:15]=2)[CH:9]=1

Participants

Reactant 2

HCID 66111Trimethylsilylacetylene

HCID 670004273-Bromo-7-difluoromethyl-5-(3-ethoxy-phenyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670003407-Difluoromethyl-5-(3-ethoxy-phenyl)-3-trimethylsilanylethynyl-pyrazolo[1,5-a]pyrimidineYield 96.1%

Procedure

Prepared from 3-bromo-7-difluoromethyl-5-(3-ethoxy-phenyl)-pyrazolo[1,5-a]pyrimidine (example C.19 step 3a) (20.0 g, 54 mmol) and commercially available trimethylsilylacetylene (15 mL, 109 mmol) as described in example C.1 step 3a to give the title compound (20 g, 95%) as a light brown solid. MS (ISP) 386 [(M+H)+].

Sources & evidence

ORD record: ord-b29387bbfca64eb8b9aa196d9404c593
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718661B2

Reaction notes

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