Trifluoroacetic acid → 6-Chloro-N-(2,3-dimethylphenyl)-2-(octylsulfanyl)pyrimidin-4-amine

HRID 637939Notes

Reaction equation

HRID 637939 reaction equation
CO[C:3]1[CH:26]=[CH:25][C:6]([CH2:7][S:8][C:9]2[N:14]=[C:13]([Cl:15])[CH:12]=[C:11]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=3[CH3:24])[N:10]=2)=[CH:5][CH:4]=1.F[C:28](F)(F)C(O)=O>>[CH2:7]([S:8][C:9]1[N:14]=[C:13]([Cl:15])[CH:12]=[C:11]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[CH3:24])[N:10]=1)[CH2:6][CH2:25][CH2:26][CH2:3][CH2:4][CH2:5][CH3:28]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 134137342-p-Methoxybenzylthio-4-chloro-6-(2,3-xylidino)-pyrimidine

Product 1

HCID 134137406-Chloro-N-(2,3-dimethylphenyl)-2-(octylsulfanyl)pyrimidin-4-amine

Procedure

To a suspension of 2-p-methoxybenzylthio-4-chloro-6-(2,3-xylidino)-pyrimidine (8 g; see example 5) in trifluoroacetic acid (80 ml) anisole (2,7 ml) is added and the mixture is refluxed for 50'. After cooling, the trifluoroacetic acid is evaporated. The residue is dissolved in ethyl ether and the separated solid is filtered, washed with ethyl ether, then with water to neutrality, with cool acetone and again with ethyl ether. 5 G of the desired product (III, 33) are obtained.

Workup

  1. additionis added
  2. temperaturethe mixture is refluxed for 50'
  3. temperatureAfter cooling
  4. customthe trifluoroacetic acid is evaporated
  5. dissolutionThe residue is dissolved in ethyl ether
  6. filtrationthe separated solid is filtered
  7. washwashed with ethyl ether

Sources & evidence

ORD record
ord-8319fd7926ec4142b96f85f1bcc80915
Source dataset
uspto-grants-1985_12
Patent number
US04559345

Reaction notes

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