Potassium Carbonate → 4-(4-Benzylpiperazin-1-yl)-2-chloropyrimidine

HRID 1699276Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 9.9 g (0.0664 mol) of 2,4-dichloropyrimidine, 200 ml of water and 11.7 ml (0.0673 mol) of 1-(phenylmethyl)piperazine was heated to 40° C. for 2 hours in an ultrasound bath. After cooling the mixture was made alkaline with potassium carbonate and extracted thoroughly with ethyl acetate. The crude product obtained after working up in the usual way was purified by column chromatography over silica gel (30-60 μm) using FM2 and FM4 (2/1 v/v) as eluant. Working up the appropriate fractions yielded 7.4 g (38.6% of theory) of a colourless oil, Rf=0.51 (FM4; Macherey-Nagel POLYGRAMO® SIL G/UV254, ready-made films for TLC).

Workup

temperatureAfter cooling the mixture
extractionextracted thoroughly with ethyl acetate

Sources & evidence

ORD record: ord-3094a39b643b4659903f62eb716630be
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06344449B1

Reaction notes

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