Chlorosuccinimide → HCID 178424306, compound

HRID 1280585Notes

Reaction equation

CS[C:3]1[N:8]=[C:7]2[NH:9][C:10](=[O:20])[N:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])[CH2:12][C:6]2=[CH:5][N:4]=1.ClN1C(=O)CCC1=O.[NH2:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([OH:36])[CH2:32][CH2:31]1>CN1CCCC1=O.O>[OH:36][C@H:33]1[CH2:34][CH2:35][C@H:30]([NH:29][C:3]2[N:8]=[C:7]3[NH:9][C:10](=[O:20])[N:11]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[CH3:19])[CH2:12][C:6]3=[CH:5][N:4]=2)[CH2:31][CH2:32]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of sulfide 10.2 (2 g) in 4 mL 1-methyl-2-pyrrolidinone was combined with N-chlorosuccinimide (1.03 g) in 4 mL 1-methyl-2-pyrrolidinone and 0.125 g water, and the mixture was stirred for 1.5 hours at 25° C. To this solution was added trans-4-aminocyclohexanol (2.65 g). The mixture was heated to 60° C. for 48 hours, cooled to 20-25° C. and treated with 10 mL water. This mixture was cooled to 5° C. and stirred for 2 hours. The solid was collected by filtration, washed with water, hexanes and dried in vacuo. The solid was purified by flash column chromatography using 95/5-90/10 dichloromethane/methanol as eluant to give 614 mg of 7-(trans-4-hydroxycyclohexylamino)-3-ortho-tolyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one. The resulting solid was converted to the hydrochloride salt by the action of ethereal hydrochloric acid/ethyl acetate on the free base.

Workup

temperatureThe mixture was heated to 60° C. for 48 hours
temperaturecooled to 20-25° C.
temperatureThis mixture was cooled to 5° C.
stirringstirred for 2 hours
filtrationThe solid was collected by filtration
washwashed with water, hexanes
customdried in vacuo
customThe solid was purified by flash column chromatography

Sources & evidence

ORD record: ord-f4d7ec0b8e044a6aa64fe1838bfddf5e
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451804B1

Reaction notes

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