Chloroform → 2-(5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazin-7-yl)-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine

HRID 917605Notes

Reaction equation

HRID 917605 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([Cl:18])[CH:11]=2)[C:5]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][N:3]=1.[N:24]1[CH:25]=[CH:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][C:28]=12.C(N(CC)CC)C.C(Cl)(Cl)Cl>C(OCC)(=O)C>[N:24]1[CH:25]=[CH:26][N:27]2[CH2:32][CH2:31][N:30]([C:2]3[N:7]=[C:6]([NH:8][CH2:9][C:10]4[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([Cl:18])[CH:11]=4)[C:5]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][N:3]=3)[CH2:29][C:28]=12

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 132470465,6,7,8-Tetrahydroimidazo(1,2-a)pyrazineHCID 226655812-Chloro-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine

Product 1

HCID 226655882-(5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazin-7-yl)-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine (prepared in Example 95) 285 mg, 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine 197 mg, triethylamine 0.22 ml and chloroform 3 ml is stirred at room temperature for 2.5 hours, followed by stirring at 60° C. for 2.5 hours. The mixture is diluted with ethyl acetate, and washed with water. The water layer is extracted with ethyl acetate, and the organic layer is washed with water and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is purified with silica gel chromatography (silica gel 10 g, solvent; chloroform:methanol=50:1) and concentrated in vacuo and triturated with isopropyl ether to give 2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine as a colorless crystalline powder, 290 mg. mp 179-182° C., MS(m/z): 443(M+H)+

Workup

  1. stirringby stirring at 60° C. for 2.5 hours
  2. washwashed with water
  3. extractionThe water layer is extracted with ethyl acetate
  4. washthe organic layer is washed with water
  5. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified with silica gel chromatography (silica gel 10 g, solvent; chloroform:methanol=50:1)
  8. concentrationconcentrated in vacuo
  9. customtriturated with isopropyl ether

Sources & evidence

ORD record
ord-59567127a86840338dac840f1ee93010
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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