1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → HCID 69449408, compound

HRID 1296726Notes

Reaction equation

HRID 1296726 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17](=[O:19])[CH3:18])=[C:15]3[N:10]([C:11]([S:20][CH3:21])=[N:12][CH:13]=[CH:14]3)[N:9]=2)=[CH:4][CH:3]=1.C(O[CH:27](OC(C)(C)C)[N:28]([CH3:30])[CH3:29])(C)(C)C>>[CH3:27][N:28]([CH3:30])/[CH:29]=[CH:18]/[C:17]([C:16]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][N:10]2[C:15]=1[CH:14]=[CH:13][N:12]=[C:11]2[S:20][CH3:21])=[O:19]

Participants

3

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 69448731HCID 69448731, compound

Product 1

HCID 69449408HCID 69449408, compoundYield 60%

Conditions

Temperature
120 °C

Procedure

To 1-[2-(4-fluorophenyl)-7-(methylsulfanyl)pyrazolo[1,5-c]pyrimidin-3-yl]ethanone (1.24 g, 4.12 mmol) was added 1,1-di-tert-butoxy-N,N-dimethylmethanamine (15 mL) and the mixture heated to 120° C. for 1 hour. The reaction was allowed to cool to room temperature and stirred for 16 hours. The mixture was diluted with hexanes. The precipitate was collected by filtration and air dried to yield (2E)-3-(dimethylamino)-1-[2-(4-fluorophenyl)-7-(methylsulfanyl)pyrazolo[1,5-c]pyrimidin-3-yl]prop-2-en-1-one (880 mg, 60%). 1H NMR (DMSO): δ 8.03 (d, 1H), 7.72–7.82 (m, 3H), 7.57 (d, 1H), 7.37 (t, 2H), 5.08 (d, 1H), 3.04 (bs, 3H), 2.71 (s, 3H), 2.52 (bs, 3H). MS m/z 357 (M+1).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe precipitate was collected by filtration and air
  3. customdried

Sources & evidence

ORD record
ord-3e2f0d1a1c4e4f7d9214f1174e5ff7dc
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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