4-Hydrazino-5,6-diphenyl-2-(trifluoromethyl)pyrimidine → 5-amino-1-[5,6-diphenyl-2-(trifluoromethyl)pyrimidin-4-yl]-3-methyl-1H-pyrazole-4-carbonitrile

HRID 1966352Notes

Reaction equation

HRID 1966352 reaction equation
CO[C:3](=[C:5]([C:8]#[N:9])[C:6]#[N:7])[CH3:4].[NH:10]([C:12]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:15]=[C:14]([C:30]([F:33])([F:32])[F:31])[N:13]=1)[NH2:11]>CO>[NH2:9][C:8]1[N:10]([C:12]2[C:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:15]=[C:14]([C:30]([F:33])([F:32])[F:31])[N:13]=2)[N:11]=[C:3]([CH3:4])[C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 100195084-Hydrazino-5,6-diphenyl-2-(trifluoromethyl)pyrimidineHCID 135128392-(1-Methoxyethylidene)malononitrile

Product 1

HCID 249623225-amino-1-[5,6-diphenyl-2-(trifluoromethyl)pyrimidin-4-yl]-3-methyl-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Methoxyethylidene malononitrile (0.17 g, 1.36 mmol) (prepared from malononitrile and triethyl orthoacetate by heating with acetic anhydride) 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 methanol (5 ml), to yield the title compound. 1H-NMR (DMSO-d6) δ: 1.97 (s, 3H), 6.97 (br, 2H, D2O exchangeable), 7.07 (d, 2H), 7.26-7.38 (m, 7H), 7.40-7.41 (m, 1H); MS m/z: 421.1 (M++1).

Workup

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

Sources & evidence

ORD record
ord-c0a1fa16bdde4ff9a4b9308b65e1e931
Source dataset
uspto-grants-2013_04
Patent number
US08420653B2

Reaction notes

Loading…