3-(2,6-Difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one → 3-(2,6-Difluoro-3,5-dimethoxy-phenyl)-7-(2,3-dihydroxy-butylamino)-1-ethyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 459981Notes

Reaction equation

HRID 459981 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[N:13]1[CH2:22][C:21]2[C:16](=[N:17][C:18](S(C)=O)=[N:19][CH:20]=2)[N:15]([CH2:26][CH3:27])[C:14]1=[O:28].[NH2:29][CH2:30][C@@H:31]([OH:35])[C@H:32]([OH:34])[CH3:33]>>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[N:13]1[CH2:22][C:21]2[C:16](=[N:17][C:18]([NH:29][CH2:30][CH:31]([OH:35])[CH:32]([OH:34])[CH3:33])=[N:19][CH:20]=2)[N:15]([CH2:26][CH3:27])[C:14]1=[O:28]

Participants

3

Reactant 2

HCID 184447943-(2,6-Difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneHCID 55291132(2R,3R)-1-Aminobutane-2,3-diol

Product 1

HCID 103438933-(2,6-Difluoro-3,5-dimethoxy-phenyl)-7-(2,3-dihydroxy-butylamino)-1-ethyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneYield 91%

Procedure

3-(2,6-Difluoro-3,5-dimethoxy-phenyl)-7-(2,3-dihydroxy-butylamino)-1-ethyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared as described in Example 7 using 0.40 g (0.97 mmol) of 3-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 0.245 g (2.33 mmol) of (2R,3R)-1-amino-butane-2,3-diol. The crude product was purified using medium-pressure chromatography eluting with 20:1 dichloromethane/methanol to give 0.40 g (91%) of title compound: mp 171° C.–173° C. MS (APCI) (m+1)/z 454.2.

Workup

  1. custom3-(2,6-Difluoro-3,5-dimethoxy-phenyl)-7-(2,3-dihydroxy-butylamino)-1-ethyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared
  2. customThe crude product was purified
  3. washeluting with 20:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-2c01f0be71844baba3685d1100132095
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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