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

HRID 1352777Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11](Cl)[N:10]=[C:9]([S:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:8]=1.[N:31]1[CH:32]=[CH:33][N:34]2[CH2:39][CH2:38][NH:37][CH2:36][C:35]=12.C(N(CC)CC)C.CN(C)C(=O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([N:37]2[CH2:38][CH2:39][N:34]3[CH:33]=[CH:32][N:31]=[C:35]3[CH2:36]2)[N:10]=[C:9]([S:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-(3-chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-chloro-2-benzylthiopyrimidine (prepared in the above (3)) 108 mg, 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine 57 mg, triethylamine 47 mg and N,N-dimethylacetamide 2.5 ml is stirred at 60° C. for 1 hour. The reaction mixture is diluted with water and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo. The residue is separated with silica gel chromatography (solvent; chloroform:methanol=200:1) to give 4-(3-chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-2-benzylthiopyrimidine as a colorless foam, 129 mg.

Workup

extractionextracted with ethyl acetate
washThe organic layer is washed
customdried
concentrationconcentrated in vacuo
customThe residue is separated with silica gel chromatography (solvent; chloroform:methanol=200:1)

Sources & evidence

ORD record: ord-8d5103f9e9654e4fb3e5164c8fb15381
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220736B2

Reaction notes

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