m-Chloroperbenzoic acid → N-(4-tert-Butylphenyl)-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydro-2-methoxypyrido[3,4-d]pyrimidin-4-amine

HRID 971235Notes

Reaction equation

C1C=C(Cl)C=C([C:8](OO)=[O:9])C=1.[C:12]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]2[C:24]3[CH2:34][CH2:33][N:32]([C:35]4[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][N:36]=4)[CH2:31][C:25]=3[N:26]=[C:27](SC)[N:28]=2)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].C[O-].[Na+]>C(O)C>[C:12]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]2[C:24]3[CH2:34][CH2:33][N:32]([C:35]4[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][N:36]=4)[CH2:31][C:25]=3[N:26]=[C:27]([O:9][CH3:8])[N:28]=2)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 60 °C

Procedure

m-CPBA (148 mg, 0.6 mmol) was added to a solution of N-(4-tert-butylphenyl)-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amine from Example 28.C. (88 mg, 0.2 mmol) in ethanol (7 mL) and stirred at room temperature for 1 hr. Solid thus formed was filtered out and dried in vacuo (50 mg). The solid was suspended in methanol (5 mL) and sodium methoxide (9 mg, 0.165 mmol) was added and stirred at 60° C. overnight. Solvent was removed in vacuo and residue was dissolved in ethyl acetate, washed with water, sodium hydrosulfite aqueous solution, brine and dried over sodium sulfate. Purified by flash chromatography to yield the product as a white solid (33 mg).

Workup

customSolid thus formed
filtrationwas filtered out
customdried in vacuo (50 mg)
customSolvent was removed in vacuo and residue
dissolutionwas dissolved in ethyl acetate
washwashed with water, sodium hydrosulfite aqueous solution, brine
dry with materialdried over sodium sulfate
customPurified by flash chromatography

Sources & evidence

ORD record: ord-a4e6d535c2d04fd0b35f4a197e8ae17c
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312330B2

Reaction notes

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