Triethylamine → 4-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-2-(4-hydroxypiperidin-1-yl)pyrimidine

HRID 1352779Notes

Reaction equation

HRID 1352779 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([N:17]2[CH2:22][CH2:21][N:20]3[CH:23]=[CH:24][N:25]=[C:19]3[CH2:18]2)[N:10]=[C:9](S(CC2C=CC=CC=2)=O)[N:8]=1.[OH:40][CH:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1.C(N(CC)CC)C>CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([N:17]2[CH2:22][CH2:21][N:20]3[CH:23]=[CH:24][N:25]=[C:19]3[CH2:18]2)[N:10]=[C:9]([N:44]2[CH2:45][CH2:46][CH:41]([OH:40])[CH2:42][CH2:43]2)[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 178483024-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-2-benzylsulfinylpyrimidine

Product 1

HCID 178483004-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-2-(4-hydroxypiperidin-1-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of whole amount of 4-(3-chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-2-benzylsulfinylpyrimidine (prepared in the above (5)), 4-hydroxypiperidine 57 mg, triethylamine 57 mg and N,N-dimethylacetamide 3 ml is stirred at 60° C. for 1.5 hours. After cooling the reaction mixture is diluted with ice water and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo. The residue is crystallized from a mixture of ethyl acetate and isopropyl ether to give of 4-(3-chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-2-(4-hydroxypiperidin-1-yl)pyrimidine as a colorless crystalline powder 75 mg.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue is crystallized from a mixture of ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-16d822288ad54651a3f5e0423e4f43ec
Source dataset
uspto-grants-2007_05
Patent number
US07220736B2

Reaction notes

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