N-methyl-2-pyrrolidone → AS-1517499

HRID 905682Notes

Reaction equation

HRID 905682 reaction equation
CN1C(=O)CCC1.[CH2:8]([NH:15][C:16]1[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=[C:18](S(C)(=O)=O)[N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[Cl:30][C:31]1[CH:32]=[C:33]([CH2:38][CH2:39][NH2:40])[CH:34]=[CH:35][C:36]=1[OH:37].C(N(C(C)C)CC)(C)C>O>[CH2:8]([NH:15][C:16]1[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:40][CH2:39][CH2:38][C:33]2[CH:34]=[CH:35][C:36]([OH:37])=[C:31]([Cl:30])[CH:32]=2)[N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 230715544-(2-Aminoethyl)-2-chlorophenol--hydrogen chloride (1/1)HCID 230715814-(Benzylamino)-2-(methanesulfonyl)pyrimidine-5-carboxamide

Product 1

HCID 10340781AS-1517499Yield 28.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To 8 ml NMP solution of 750 mg of 4-benzylamino-2-methylsulfonylpyrimidine-5-carboxamide were added 765 mg of 2-(3-chloro-4-hydroxyphenyl)ethylamine hydrochloride and 1.07 ml of diisopropylethylamine, followed by stirring a 110° 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:aqueous ammonia) and the resulting crude crystals were recrystallized (methanol-ethyl acetate) to obtain 280 mg of 4-benzylamino-2-{[2-(3-chloro-4-hydroxyphenyl)ethyl]amino}pyrimidine-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:aqueous ammonia)
  6. customthe resulting crude crystals were recrystallized (methanol-ethyl acetate)

Sources & evidence

ORD record
ord-979c4cb877124a5ca40ec941e90ff027
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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