Hydrochloric Acid → HCID 178432390, compound

HRID 1348549Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10](=O)[CH2:11]C(OCC)=O.[ClH:18].[NH2:19][C:20]1[NH:21][CH:22]=[CH:23][N:24]=1.[CH2:25]1CN2C(=NCCC2)C1.Cl.[OH2:35]>C(Cl)(Cl)Cl.CN(C)C=O>[OH:35][C:25]1[N:21]2[CH:22]=[CH:23][N:24]=[C:20]2[N:19]=[C:10]([CH3:11])[C:9]=1[C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:18]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1.29 g of ethyl (2-chloro-6-fluorophenyl)acetoacetate, 0.60 g of aminoimidazole hydrochloride, 1.24 g of 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) and 5 ml of N,N-dimethylformamide was heated at 100° C. for 14 hours. The reaction mixture was allowed to cool, and chloroform and water were added thereto. To the separated water layer, conc. hydrochloric acid was added and the precipitate was filtered, which was followed to subject to silica gel chromatography to give 0.16 g of 5-hydroxy-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine.

Workup

temperatureto cool
filtrationthe precipitate was filtered

Sources & evidence

ORD record: ord-7054545e715948659e3fcd2f805a7e49
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211545B2

Reaction notes

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