Ethyl (2-chloroacetyl)carbamate → (7-Chloro-imidazo[1,2-c]pyrimidin-2-yl)-carbamic acid ethyl ester

HRID 229358Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.Cl[CH2:10][C:11]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=O>CN1CCN(C)C1=O>[CH2:17]([O:16][C:14](=[O:15])[NH:13][C:11]1[N:1]=[C:2]2[CH:3]=[C:4]([Cl:8])[N:5]=[CH:6][N:7]2[CH:10]=1)[CH3:18]

Participants

Conditions

Temperature: 130 °C

Procedure

A solution of 6-amino-4-chloropyrimidine (1) (0.504 g, 3.89 mmol) and N-chloroacetylurethane (0.770 g, 4.65 mmol) in 1,3-dimethyl-2-imidazolidinone (10 mL) was heated to 130° C. under nitrogen for 3 h. N-Chloroacetylurethane (0.770 g, 4.65 mmol) was added and the mixture was heated to 130° C. under nitrogen for a further 3.5 h. The black oily solution was poured onto ice (200 g) and the aqueous solution was extracted with ethyl acetate (3×250 mL). The organic fractions were combined, removal of solvent in vacuo gave an oily solid which was triturated with ether. Filtration of the solid and washing with ether gave urethane (2) (88 mg, 9%) as a solid. APCI-MS Found [M+H]+=241, 243.

Workup

additionThe black oily solution was poured onto ice (200 g)
extractionthe aqueous solution was extracted with ethyl acetate (3×250 mL)
customremoval of solvent in vacuo
customgave an oily solid which
customwas triturated with ether
filtrationFiltration of the solid
washwashing with ether

Sources & evidence

ORD record: ord-784c24e7e9484ec087a016e91ccf7e1d
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563788B2

Reaction notes

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