1,2-Dichloroethane → (E)-N-(azetidin-3-yloxy)-1-pyrimidin-2-ylpropan-2-imine;hydrochloride

HRID 82959Notes

Reaction equation

C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([O:12]/[N:13]=[C:14](\[CH3:22])/[CH2:15][C:16]3[N:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:9]2)C=CC=CC=1.[Cl:29]CCCl.ClC(OC(Cl)=O)C>CO>[ClH:29].[NH:8]1[CH2:11][CH:10]([O:12]/[N:13]=[C:14](\[CH3:22])/[CH2:15][C:16]2[N:17]=[CH:18][CH:19]=[CH:20][N:21]=2)[CH2:9]1

Participants

Conditions

Temperature: 70 °C

Procedure

A 25 mL flask was charged with (2E)-1-pyrimidin-2-ylacetone O-(1-diphenylmethylazetidin-3-yl)oxime (372 mg, 1.0 mmol; which may be prepared as described in Step 4) and 1,2-dichloroethane (8.8 mL). 1-Chloroethylchloroformate (576 μL, 5.28 mmol) was added and the reaction mixture was heated to 70° C. for 3 h. After cooling to room temperature, methanol (8.8 mL) was added and the reaction mixture was heated to 70° C. for 3 h. The reaction mixture was concentrated to dryness and the crude mixture triturated in pentane and diethyl ether to give the title compound (240 mg, 99%) as a dark solid.

Workup

temperatureAfter cooling to room temperature
temperaturethe reaction mixture was heated to 70° C. for 3 h
concentrationThe reaction mixture was concentrated to dryness
customthe crude mixture triturated in pentane

Sources & evidence

ORD record: ord-e823a322f7184b669973fc63df7cf5fd
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846711B2

Reaction notes

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