Methyl p-toluenesulfonate → HCID 86622930, compound

HRID 1014961Notes

Reaction equation

[CH:1]1[N:2]=[CH:3][N:4]2[C:9]=1[CH2:8][CH2:7][NH:6][C:5]2=[O:10].[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O:21]C)(=[O:20])=[O:19])=[CH:14][CH:13]=1>CN(C=O)C>[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([S:18]([O-:21])(=[O:20])=[O:19])=[CH:16][CH:17]=1.[CH3:11][N+:2]1[CH:1]=[C:9]2[N:4]([C:5](=[O:10])[NH:6][CH2:7][CH2:8]2)[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred suspension of 7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one (699.7 g) in DMF 2.45 litres) was heated to ca. 60° C. A solution of methyl 4-methylbenzenesulfonate (1058.2 g.) in DMF (0.7 litres) was added over 100 min at ca. 60° C., and rinsed in with DMF (0.35 litres). The white suspension was stirred at ca. 60° C. for 200 min. when the reaction was complete by nmr. The reaction mixture was allowed to cool to ca. 40° C. and TBME (5.25 litres) was added. The product was cooled to ca. 22° C., aged at this temperature for 17 h, and filtered. The cake was washed with TBME-DMF (3:1, 1.4 litres), then with TBME (2×1.4 litres), the cake was pulled dry, and the product was dried in vacuo at ca. 50° C. to yield the title compound, 1583.5 g.

Workup

washrinsed in with DMF (0.35 litres)
temperatureto cool to ca. 40° C.
additionTBME (5.25 litres) was added
temperatureThe product was cooled to ca. 22° C.
waitaged at this temperature for 17 h
filtrationfiltered
washThe cake was washed with TBME-DMF (3:1, 1.4 litres)
dry with materialwith TBME (2×1.4 litres), the cake was pulled dry
customthe product was dried in vacuo at ca. 50° C.

Sources & evidence

ORD record: ord-d7b2cb81884e4eb19e8e6ec34c20f1d4
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985740B2

Reaction notes

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