Ethyl 3,3-Bis(methylthio)-2-cyanoacrylate → ethyl 5-amino-1-[5,6-diphenyl-2-(trifluoromethyl)pyrimidin-4-yl]-3-(methylthio)-1H-pyrazole-4-carboxylate

HRID 72686Notes

Reaction equation

HRID 72686 reaction equation
[C:1]([C:3](=[C:9](SC)[S:10][CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[NH:14]([C:16]1[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:20]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:19]=[C:18]([C:34]([F:37])([F:36])[F:35])[N:17]=1)[NH2:15]>CO>[NH2:2][C:1]1[N:14]([C:16]2[C:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[C:20]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:19]=[C:18]([C:34]([F:37])([F:36])[F:35])[N:17]=2)[N:15]=[C:9]([S:10][CH3:11])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 2747745Ethyl 3,3-Bis(methylthio)-2-cyanoacrylateHCID 100195084-Hydrazino-5,6-diphenyl-2-(trifluoromethyl)pyrimidine

Product 1

HCID 24962323ethyl 5-amino-1-[5,6-diphenyl-2-(trifluoromethyl)pyrimidin-4-yl]-3-(methylthio)-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-cyano-3,3-bis(methylthio)acrylate (0.3 g, 1.36 mmol) was heated with 4-hydrazino-5,6-diphenyl-2-(trifluoromethyl)pyrimidine (0.15 g, 0.45 mmol) in methanol (6 ml) overnight at 60-65° C. The solid that separated out from the reaction mixture was filtered and washed with isopropylalcohol (5 ml), to furnish the required compound. 1H-NMR (DMSO-d6) δ: 1.22-1.25 (t, 3H), 3.16 (s, 3H), 4.11-4.17 (q, 2H), 4.36 (br, 2H, D2O exchangeable), 7.12 (d, 2H), 7.25-7.35 (m, 7H), 7.69 (d, 1H); MS m/z: 500.1 (M++1).

Workup

  1. customThe solid that separated out from the reaction mixture
  2. filtrationwas filtered
  3. washwashed with isopropylalcohol (5 ml)

Sources & evidence

ORD record
ord-56db3586ff254b6b960a2b247ae3dc9f
Source dataset
uspto-grants-2014_09
Patent number
US08828999B2

Reaction notes

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