N-bromobutanimide → HCID 178499064, compound

HRID 1172055Notes

Reaction equation

HRID 1172055 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([OH:11])[N:8]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH3:20])[C:13]=2[F:21])[N:6]=1)=[O:4].[Br:22]N1C(=O)CCC1=O>ClCCl.C(#N)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([Br:22])=[C:9]([OH:11])[N:8]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH3:20])[C:13]=2[F:21])[N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 178498593HCID 178498593, compound

Product 1

HCID 178499064HCID 178499064, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

6-Hydroxy-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid methyl ester(150 mg, 0.48 mmol) was combined with N-bromosuccinimide (180 mg, 1.0 mmol) in 7 mL dichloromethane plus 2 mL acetonitrile and heated to reflux for 2 hours. After cooling the volatiles were removed under vacuum and the residue was taken up in 15 mL dichloromethane plus 5 mL water. The organic phase was separated and washed with 10 mL 5% sodium bisulfite solution, washed with 10 mL brine, dried and evaporated to give 120 mg (63% yield) of 6-hydroxy-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-bromopyrimidine-4-carboxylic acid methyl ester: mp 192-195° C.; MS m/z 390/392; 1H NMR (DMSO-d6): δ 7.47 (m, 3H), 3.95 (d, 3H), 3.91 (s, 3H)

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling the volatiles
  4. customwere removed under vacuum
  5. customThe organic phase was separated
  6. washwashed with 10 mL 5% sodium bisulfite solution
  7. washwashed with 10 mL brine
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-7f031c453f1c4a8ba5d8bebb11b480b7
Source dataset
uspto-grants-2010_11
Patent number
US07833940B2

Reaction notes

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