Bromine → HCID 90408691, compound

HRID 516572Notes

Reaction equation

HRID 516572 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Si](C)(C)C)=[C:10]([F:18])[C:9]=2[F:19])[N:5]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:3]=1[O:24][CH3:25].[Br:26]Br.S(=O)(O)[O-].[Na+]>ClCCCl.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Br:26])=[C:10]([F:18])[C:9]=2[F:19])[N:5]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:3]=1[O:24][CH3:25]

Participants

6

Reactant 3

HCID 24408BromineHCID 23665763Sodium BisulfiteHCID 90408427HCID 90408427, compound

Product 1

HCID 90408691HCID 90408691, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 6-amino-2-(2,3-difluoro-4-(trimethylsilyl)phenyl)-5-methoxypyrimidine-4-carboxylate (350 mg, 0.95 mmol) was stirred in 4 mL 1,2-dichloroethane, treated with bromine (1.0 g, 6.3 mmol) and heated to 60° C. for 6 h. After cooling, the mixture was stirred with 15% sodium bisulfite solution until negative to starch-iodine paper. The mixture was diluted with ethyl acetate, washed with saturated NaCl, dried (Na2SO4), and evaporated. Purification by flash chromatography (SiO2, eluting with 0-30% ethyl acetate in hexanes) provided the title compound as white solid (75 mg, 23%).

Workup

  1. temperatureAfter cooling
  2. washwashed with saturated NaCl
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customPurification
  6. washby flash chromatography (SiO2, eluting with 0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-407ecba1b4c8443e8f425f7f5bd79a7e
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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