Phosphorus oxychloride → 5-Bromo-4-chloro-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine

HRID 238246Notes

Reaction equation

HRID 238246 reaction equation
[Br:1][C:2]1[C:3](=O)[NH:4][C:5]([CH:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)[CH3:9])=[N:6][CH:7]=1.P(Cl)(Cl)([Cl:30])=O>>[Br:1][C:2]1[C:3]([Cl:30])=[N:4][C:5]([CH:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)[CH3:9])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 599931295-Bromo-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-pyrimidin-4-one

Product 1

HCID 865970915-Bromo-4-chloro-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine

Conditions

Temperature
90 °C

Procedure

In a flask containing of 5-bromo-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-pyrimidin-4-one (150.0 mg, 0.33 mmol) in phosphorus oxychloride (2 ml) was heated to 90° C. for 2 hours, then the solvent was concentrated under reduced pressure to give the 5-bromo-4-chloro-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine that was used in the next step without any purification. MS m/z calc. 524.2 found (ESI); 526.2 (M+1)+. Retention time 2.91 minutes.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-55492101b68849318d2cd17203962dd7
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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