Guanidine, 1,1-dimethyl-, sulfate → 4-Amino-2(-N,N-dimethylamino)-5-(2,3,5-trichlorophenyl)-6-trifluoromethyl pyrimidine

HRID 234922Notes

Reaction equation

HRID 234922 reaction equation
CC[O-].[Na+].S(O)(O)(=O)=O.[CH3:10][N:11]([CH3:15])[C:12]([NH2:14])=[NH:13].[Cl:16][C:17]1[C:22]([Cl:23])=[CH:21][C:20]([Cl:24])=[CH:19][C:18]=1[C:25](=[C:28](OC)[C:29]([F:32])([F:31])[F:30])[C:26]#[N:27]>CCO>[NH2:27][C:26]1[C:25]([C:18]2[CH:19]=[C:20]([Cl:24])[CH:21]=[C:22]([Cl:23])[C:17]=2[Cl:16])=[C:28]([C:29]([F:32])([F:31])[F:30])[N:14]=[C:12]([N:11]([CH3:15])[CH3:10])[N:13]=1

Participants

5

Reactant 3

HCID 220673Guanidine, 1,1-dimethyl-, sulfateHCID 2723922Sodium ethoxideHCID 544228532-(2,3,5-Trichlorophenyl)-4,4,4-trifluoro-3-methoxybut-2-enonitrile

Product 1

HCID 115238784-Amino-2(-N,N-dimethylamino)-5-(2,3,5-trichlorophenyl)-6-trifluoromethyl pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of NaOEt (from 0.144 g of Na) in EtOH (12.5 ml) was added 1,1-dimethylguanidine sulphate (1.4 g), (Aldrich). The resulting white suspension was stirred at room temperature for 10 minutes. A solution of 2-(2,3,5-trichlorophenyl)-4,4,4-trifluoro-3-methoxybut-2-enonitrile (see Example 1.6) (0.85 g) in EtOH (2.5 ml) was added and the resulting mixture was stirred at reflux for 4.5 hours. After cooling, the suspension was filtered, and the filtrate was evaporated to dryness in vacuo. Chromatography on silica gel, eluting with CHCl3, gave the desired product, 0.61 g, mp. 124°-126° C.

Workup

  1. stirringthe resulting mixture was stirred
  2. temperatureat reflux for 4.5 hours
  3. temperatureAfter cooling
  4. filtrationthe suspension was filtered
  5. customthe filtrate was evaporated to dryness in vacuo
  6. washChromatography on silica gel, eluting with CHCl3

Sources & evidence

ORD record
ord-9ebc8bb0460d4ba8ba9626ee94e009e2
Source dataset
uspto-grants-1997_01
Patent number
US05597827

Reaction notes

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