4-Aminotetrahydropyran → 3-(2-chlorophenyl)-7-(tetrahydropyran-4-ylamino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1280568Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13](S(CC3C=CC=CC=3)(=O)=O)=[N:14][CH:15]=2)[NH:10][C:9]1=[O:28].[NH2:29][CH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([NH:29][CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[N:14][CH:15]=2)[NH:10][C:9]1=[O:28]

Participants

Conditions

Temperature: 100 °C

Procedure

Sulfone 9.1 (0.205 g, 0.494 mmol) in 5 mL 1-methyl-2-pyrrolidinone was combined with 4-aminotetrahydropyran (0.100 g, 0.988 mmol). The reaction was stirred at 100° C. for 24 hours and purified by column chromatography on silica gel using 3-7% methanol/dichloromethane as eluant. The column fractions containing product were combined and concentrated in vacuo to a give the title compound as a brown gum which was redissolved in methanol. Addition of hydrochloric acid (1.0M/Et2O, 1.0 equivalent) gave 0.026 g of the hydrochloride salt 3-(2-chlorophenyl)-7-(tetrahydropyran-4-ylamino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one.

Workup

custompurified by column chromatography on silica gel using 3-7% methanol/dichloromethane as eluant
additionThe column fractions containing product
concentrationconcentrated in vacuo to

Sources & evidence

ORD record: ord-45d93574da214161ab0a0abea17710dc
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451804B1

Reaction notes

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