Chlorosuccinimide → HCID 67427941, compound

HRID 869290Notes

Reaction equation

HRID 869290 reaction equation
[OH:1][C:2]1[C:3](=[O:22])[N:4]([CH3:21])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[Cl:23]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:23][C:7]1[N:6]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:12][CH:13]=2)[N:4]([CH3:21])[C:3](=[O:22])[C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 67407367HCID 67407367, compound

Product 1

HCID 67427941HCID 67427941, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 50 mg (0.170 mmol) 5-hydroxy-3-methyl-2-(4-phenoxyphenyl)pyrimidin-4(3H)-one in 850 μl CH2Cl2 was added 23.8 mg (0.178 mmol) N-chlorosuccinimide. The reaction mixture was heated to 50° C. for 12 h, then cooled to rt, and concentrated in vacuo. Purification by HPLC gave 10.0 mg (18% yield) of 6-chloro-5-hydroxy-3-methyl-2-(4-phenoxyphenyl)pyrimidin-4(3H)-one. 1H NMR δ (ppm) (CDCl3): 7.48-7.46 (2H, m), 7.41-7.38 (2H, m), 7.19 (1H, d, J=7.56 Hz), 7.09-7.05 (4H, m), 6.43 (1H, bs), 3.56 (3H, s). FIRMS (ESI positive) calc (M+H)+=329.0687 found 329.0693.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated in vacuo
  3. customPurification by HPLC

Sources & evidence

ORD record
ord-ad5e85abeafe4fa9a09fbfc3fe1673a7
Source dataset
uspto-grants-2015_03
Patent number
US08969364B2

Reaction notes

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