Ammonia → HCID 22732502, compound

HRID 1765268Notes

Reaction equation

HRID 1765268 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1.[F:15][C:16]([F:26])([F:25])[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][NH2:21].Cl.N>O>[CH3:8][C:6]1[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=[C:2]([NH:21][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[C:17]([C:16]([F:15])([F:25])[F:26])[CH:18]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 759623-(Trifluoromethyl)benzylamineHCID 27633954-Chloro-6-methyl-2-(pyridin-2-yl)pyrimidine

Product 1

HCID 22732502HCID 22732502, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-6-methyl-2-(2-pyridinyl)pyrimidine (82.3 mg, 0.4 mmol), 3-trifluoromethylbenzylamine (70.1 mg, 0.4 mmol), water (5 ml) and 2N HCl (300 μl) was refluxed for two days. The resulting solution was basified to pH ˜11 with ammonia and extracted with ethyl acetate (10 ml×3). The combined ethyl acetate extracts were dried with sodium sulfate, and evaporated under vacuum. The residue was purified by column chromatography (hexane/ethyl acetate: 1/1) to give the title compound as a solid (34 mg, 25%). 1H NMR (CD3OD): 8.59 (d, J=4.2 Hz, 1H), 8.27 (m, 2H), 7.86 (m, 2H), 7.43 (m, 2H), 6.18 (s, 2H), 4.76 (s, 2H), 2.26 (s, 3H).

Workup

  1. temperaturewas refluxed for two days
  2. extractionextracted with ethyl acetate (10 ml×3)
  3. dry with materialThe combined ethyl acetate extracts were dried with sodium sulfate
  4. customevaporated under vacuum
  5. customThe residue was purified by column chromatography (hexane/ethyl acetate: 1/1)

Sources & evidence

ORD record
ord-6854dca8a4614d7da242644ce2cc7352
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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