Diglycolamine → HCID 10342916, compound

HRID 459992Notes

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][O:31][CH2:32][CH2:33][OH:34]>>[CH2:1]([N:3]1[C:8]2=[N:9][C:10]([NH:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][OH:34])=[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

Reactant 2

HCID 13578Diglycolamine

HCID 18445054HCID 18445054, compound

Product 1

HCID 10342916HCID 10342916, compound

Procedure

1-Ethyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-[2-(2-hydroxy-ethoxy)-ethylamino]-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared as in Example 2 using 0.350 g (0.887 mmol) 1-ethyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 0.267 mL (2.66 mmol) 2-(2-amino-ethoxy)-ethanol. The final product was purified by column chromatography (20:1 dichloromethane/methanol). This gave 0.331 g (86%) of 1-ethyl-3-(2-fluoro-3,5-dimethoxy-phenyl)-7-[2-(2-hydroxy-ethoxy)-ethylamino]-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a white solid: mp 143° C.–146° C.; MS (APCI) m+1/z 436.

Workup

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

Sources & evidence

ORD record: ord-313bb3f190194df1852d188a3f8d9276
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196090B2

Reaction notes

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