Morpholine → HCID 69370781, compound

HRID 431054Notes

Reaction equation

HRID 431054 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=2)[C:11]([C:25](=[O:28])[CH:26]=[CH2:27])=[CH:10][N:9]=1.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>C(O)C>[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=2)[C:11]([C:25]([CH2:26][CH2:27][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:28])=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 69369766HCID 69369766, compound

Product 1

HCID 69370781HCID 69370781, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-(acryloyl)pyrimidine (72 mg) in ethanol (2 ml) is added morpholine (78 μl) at room temperature, and the mixture is stirred at room temperature for 40 minutes. The reaction mixture is concentrated under reduced pressure, and the residue is poured into water, and the mixture is extracted with ethyl acetate. The organic layer is washed successively with water and brine, dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure to give (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[(2-morpholinoethyl)carbonyl]-pyrimidine (91 mg).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additionthe residue is poured into water
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic layer is washed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a137720ab626445985e41d9d35c0f2f2
Source dataset
uspto-grants-2003_12
Patent number
US06656935B2

Reaction notes

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