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

HRID 917606Notes

Reaction equation

HRID 917606 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH2:9][CH2:8][N:7]([C:10]3[N:15]=[C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([Cl:26])[CH:19]=4)[C:13]([C:27]([O:29]CC)=[O:28])=[CH:12][N:11]=3)[CH2:6][C:5]=12.[OH-].[Na+].O1CCCC1>CS(C)=O.O>[N:1]1[CH:2]=[CH:3][N:4]2[CH2:9][CH2:8][N:7]([C:10]3[N:15]=[C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([Cl:26])[CH:19]=4)[C:13]([C:27]([OH:29])=[O:28])=[CH:12][N:11]=3)[CH2:6][C:5]=12

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 226655882-(5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazin-7-yl)-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine

Product 1

HCID 226655502-(5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazin-7-yl)-4-(3-chloro-4-methoxybenzylamino)-5-carboxypyrimidine

Reagents, catalysts & solvents 1

HCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Procedure

2-(5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazin-7-yl)-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine (prepared in Example 97) 290 mg and 2N aqueous sodium hydroxide solution 1.64 ml are suspended in dimethyl sulfoxide-water (5 ml:1 ml) and stirred at room temperature for 1 hour. Tetrahydrofuran 5 ml is added thereto and the mixture is stirred at room temperature for 13 hours. After removal of tetrahydrofuran in vacuo, the residue is diluted with water and neutralized with a 10% aqueous citric acid solution. The precipitate is collected, washed with water, methanol and isopropyl ether to give 2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-4-(3-chloro-4-methoxybenzylamino)-5-carboxypyrimidine as a colorless crystalline powder, 187 mg. mp 223-226° C. (decomposition), MS(m/z): 413(M−H)−

Workup

  1. stirringthe mixture is stirred at room temperature for 13 hours
  2. customAfter removal of tetrahydrofuran in vacuo
  3. additionthe residue is diluted with water
  4. customThe precipitate is collected
  5. washwashed with water, methanol and isopropyl ether

Sources & evidence

ORD record
ord-348c6ed5167443b19c102aecef5a2907
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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