Serinol → 1-cyclopentyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-(2-hydroxy-1-hydroxymethyl-ethylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 459987Notes

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.[NH2:31][CH:32]([CH2:35][OH:36])[CH2:33][OH:34]>>[CH:1]1([N:6]2[C:11]3=[N:12][C:13]([NH:31][CH:32]([CH2:35][OH:36])[CH2:33][OH:34])=[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

Reactant 2

HCID 68294Serinol

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

Product 1

HCID 99817481-cyclopentyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-(2-hydroxy-1-hydroxymethyl-ethylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

Procedure

1-Cyclopentyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-(2-hydroxy-1-hydroxymethyl-ethylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared as in Example 2 using 0.4 g (0.92 mmol) 1-cyclopentyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 0.25 g (2.76 mmol) serinol. The final product was purified by column chromatography (20:1 dichloromethane/methanol). This gave 0.29 g (68%) of 1-cyclopentyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-(2-hydroxy-1-hydroxymethyl-ethylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a white solid: mp 194° C.–195° C.; MS (APCI) m/z 462.2, 463.2.

Workup

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

Sources & evidence

ORD record: ord-fc85c6e149cb4c899e8e4fc541993e79
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196090B2

Reaction notes

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