3-(2-(4-Fluorophenyl)acetyl)dihydro-2H-thiopyran-4(3H)-one → 4-(4-Fluorobenzyl)-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine

HRID 1930628Notes

Reaction equation

HRID 1930628 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH:11]2[C:16](=O)[CH2:15][CH2:14][S:13][CH2:12]2)=O)=[CH:4][CH:3]=1.[CH3:18][C:19]1[N:20]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH2:33])=[NH:32])=[CH:26][CH:25]=2)[CH:21]=[CH:22][N:23]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:11]3[CH2:12][S:13][CH2:14][CH2:15][C:16]=3[N:33]=[C:31]([NH:30][C:27]3[CH:28]=[CH:29][C:24]([N:20]4[CH:21]=[CH:22][N:23]=[C:19]4[CH3:18])=[CH:25][CH:26]=3)[N:32]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 593337083-(2-(4-Fluorophenyl)acetyl)dihydro-2H-thiopyran-4(3H)-oneHCID 178432900HCID 178432900, compound

Product 1

HCID 593337504-(4-Fluorobenzyl)-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amineYield 78%

Procedure

4-(4-Fluorobenzyl)-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine (103 mg, 78%) was synthesised from 3-(2-(4-fluorophenyl)acetyl)dihydro-2H-thiopyran-4(3H)-one and 1-(4-(2-methyl-1H-imidazol-1-yl)phenyl)guanidine (Example 41c) according to the general procedure for the synthesis of pyrimidines. MS (ES+) m/z 432.2 (M+H)+

Sources & evidence

ORD record
ord-b60d3dfa177147fcb8cc3997c10f5419
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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