(S,S)-1,4-diamino-butane-2,3-diol → 7-(4-Amino-2,3-dihydroxy-butylamino)-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 459979Notes

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:36])[C@@H:32]([OH:35])[CH2:33][NH2:34]>>[NH2:29][CH2:30][CH:31]([OH:36])[CH:32]([OH:35])[CH2:33][NH:34][C:18]1[N:17]=[C:16]2[N:15]([CH2:26][CH3:27])[C:14](=[O:28])[N:13]([C:3]3[C:2]([F:1])=[C:7]([O:8][CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=3[F:12])[CH2:22][C:21]2=[CH:20][N:19]=1

Participants

Reactant 2

HCID 11789191(S,S)-1,4-diamino-butane-2,3-diol

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

Product 1

HCID 100048217-(4-Amino-2,3-dihydroxy-butylamino)-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneYield 43%

Procedure

7-(4-Amino-2,3-dihydroxy-butylamino)-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared as in Example 2 using 0.5 g (1.2 mmol) 3-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 0.433 g (3.6 mmol) (S,S)-1,4-diamino-butane-2,3-diol. The final product was purified by column chromatography (40:6:1 dichloromethane/methanol/sat. aqueous ammonium hydroxide solution) which gave 0.24 g (43%) of the final product as a white solid: mp 115° C. (dec.); MS (APCI) m/z 469.1, 470.2.

Workup

customThe final product was purified by column chromatography (40:6:1 dichloromethane/methanol/sat. aqueous ammonium hydroxide solution) which

Sources & evidence

ORD record: ord-81606a908f7e4e5b98f09fd9a3d57887
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196090B2

Reaction notes

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