1-cyclopentyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one → HCID 178493523, compound

HRID 459993Notes

Reaction equation

HRID 459993 reaction equation
[CH:1]1([N:6]2[C:11]3=[N:12][C:13](S(C)=O)=[N:14][CH:15]=[C:10]3[CH2:9][N:8]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[C:20]=3[F:29])[C:7]2=[O:30])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([NH2:38])[CH2:34][CH2:33]1>>[CH:1]1([N:6]2[C:11]3=[N:12][C:13]([NH:38][C@H:35]4[CH2:36][CH2:37][C@H:32]([OH:31])[CH2:33][CH2:34]4)=[N:14][CH:15]=[C:10]3[CH2:9][N:8]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[C:20]=3[F:29])[C:7]2=[O:30])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 184448451-cyclopentyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneHCID 178511715HCID 178511715, compound

Product 1

HCID 178493523HCID 178493523, compound

Procedure

1-Cyclopentyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-(trans-4-hydroxy-cyclohexylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared as in Example 2 using 0.5 g (1.15 mmol) 1-cyclopentyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 0.389 g (3.45 mmol) trans-4-hydroxy-cyclohexylamine. The final product was purified by column chromatography (20:1 dichloromethane/ methanol). This gave 0.320 g (57%) of 1-cyclopentyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-(trans-4-hydroxy-cyclohexylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a white solid: mp 108° C.–110° C.; MS (APCI) m/z 486.2, 487.2.

Workup

  1. customThe final product was purified by column chromatography (20:1 dichloromethane/ methanol)

Sources & evidence

ORD record
ord-0830e60450b94627b12f56e4a7626f6e
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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