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

HRID 1782735Notes

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 POLYGRAM® SIL G/UV254, ready-made films for TLC).

Workup

temperatureAfter cooling the mixture
extractionextracted thoroughly with ethyl acetate

Sources & evidence

ORD record: ord-1a6e715cfecd4e3a803bf7a5a91ec135
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498325B2

Reaction notes

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