Methanol → HCID 10435141, compound

HRID 459984Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:17]3=[N:18][C:19]([NH:22][CH3:23])=[N:20][CH:21]=[C:16]3[CH2:15][N:14]([C:24]3[C:29]([F:30])=[C:28]([O:31][CH3:32])[CH:27]=[C:26]([O:33][CH3:34])[C:25]=3[F:35])[C:13]2=[O:36])[CH2:8][CH2:7]1)=[O:5])C.CO.[OH-].[Na+]>O>[F:35][C:25]1[C:26]([O:33][CH3:34])=[CH:27][C:28]([O:31][CH3:32])=[C:29]([F:30])[C:24]=1[N:14]1[CH2:15][C:16]2[C:17](=[N:18][C:19]([NH:22][CH3:23])=[N:20][CH:21]=2)[N:12]([CH:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)[C:13]1=[O:36]

Participants

Conditions

Temperature: 50 °C

Procedure

To a 250-mL round-bottomed flask was added Ethyl-4-[3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-methylamino-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-cyclohexanecarboxylate (crude 1.5 mmol), methanol (70 mL), water (20 mL), and sodium hydroxide (600 mg, 15 mmol), and the mixture was heated to 50° C. for 3 days. The crude reaction solution was then concentrated to less than 10 mL in vacuo, and then the volume was increased to 50 mL with water. The pH was then adjusted to 4 with 6 M hydrochloric acid, and the resulting white precipitate was collected by filtration and dried in vacuo overnight to deliver the title compound (460 mg, 63% yield for 2 steps) as a white solid: mp 148° C., LRMS: 478.2 (M+H).

Workup

customThe crude reaction solution
concentrationwas then concentrated to less than 10 mL in vacuo
temperaturethe volume was increased to 50 mL with water
filtrationthe resulting white precipitate was collected by filtration
customdried in vacuo overnight

Sources & evidence

ORD record: ord-a07f60c20a0b4e85b7f468416f47403f
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196090B2

Reaction notes

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