Cyclohexylamine → HCID 44422660, compound

HRID 905690Notes

Reaction equation

HRID 905690 reaction equation
CN1C(=O)CCC1.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18]2[N:23]=[C:22](S(C)=O)[C:21]([C:27]([NH2:29])=[O:28])=[CH:20][N:19]=2)=[CH:11][CH:10]=1.[CH:30]1([NH2:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(N(C(C)C)CC)(C)C>O>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18]2[N:23]=[C:22]([NH:36][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:21]([C:27]([NH2:29])=[O:28])=[CH:20][N:19]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 67388067HCID 67388067, compound

Product 1

HCID 44422660HCID 44422660, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 8 ml portion of NMP solution containing 800 mg of 2-{[2-(4-hydroxyphenyl)ethyl]amino}-4-(methylsulfinyl)pyrimidine-5-carboxamide was mixed with 373 mg of cyclohexylamine and 0.87 ml of diisopropylethylamine, followed by stirring at 100° C. for 1 hour. The reaction mixture was cooled down to room temperature, and then mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (chloroform:methanol), and the resulting crude crystals were recrystallized (methanol-ethyl acetate) to obtain 547 mg of 2-{[2-(4-hydroxyphenyl)ethyl]amino}-4-cyclohexylaminopyrimidine-5-carboxamide as colorless crystals.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customThe resulting residue was purified by a silica gel column chromatography (chloroform:methanol)
  6. customthe resulting crude crystals were recrystallized (methanol-ethyl acetate)

Sources & evidence

ORD record
ord-2799992926eb441b9c6c41d7a039eb40
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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