4-Amino-1-butanol → HCID 10002154, compound

HRID 459988Notes

Reaction equation

HRID 459988 reaction equation
[CH2:1]([N:3]1[C:8]2=[N:9][C:10](S(C)=O)=[N:11][CH:12]=[C:7]2[CH2:6][N:5]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[C:17]=2[F:26])[C:4]1=[O:27])[CH3:2].[NH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33]>>[CH2:1]([N:3]1[C:8]2=[N:9][C:10]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33])=[N:11][CH:12]=[C:7]2[CH2:6][N:5]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[C:17]=2[F:26])[C:4]1=[O:27])[CH3:2]

Participants

3

Reactant 2

HCID 258684-Amino-1-butanolHCID 18445054HCID 18445054, compound

Product 1

HCID 10002154HCID 10002154, compound

Procedure

1-Ethyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-(4-hydroxy-butylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared as in Example 2 using 0.4 g (1.01 mmol) 1-ethyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 0.27 g (3.03 mmol) 4-amino-butan-1-ol. The final product was purified by column chromatography (20:1 dichloromethane/methanol). This gave 0.375 g (88%) of 1-ethyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-(4-hydroxy-butylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a white solid: mp 129° C.–131° C.; MS (APCI) m+1/z 420.

Workup

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

Sources & evidence

ORD record
ord-09cf7681267842a4ab0715e4ca368efb
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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