Iodine chloride → HCID 90410528, compound

HRID 516566Notes

Reaction equation

HRID 516566 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].[I:26]Cl>ClCCCl.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([I: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

5

Reactant 2

HCID 24640Iodine chlorideHCID 90408427HCID 90408427, compound

Product 1

HCID 90410528HCID 90410528, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 6-amino-2-(2,3-difluoro-4-(trimethylsilyl)phenyl)-5-methoxypyrimidine-4-carboxylate (330 mg, 0.90 mmol) was stirred in 1,2-dichloroethane (5 mL), treated with iodine monochloride (1.0 g, 6.9 mmol), and heated to 70° C. for 21 h. After cooling, the mixture was diluted with ethyl acetate, washed with 15% sodium bisulfite, washed with saturated NaCl, dried (Na2SO4), and evaporated. The material was purified by RP-HPLC using 70% acetonitrile to provide the title compound as a white solid (250 mg, 66%).

Workup

  1. temperatureAfter cooling
  2. washwashed with 15% sodium bisulfite
  3. washwashed with saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe material was purified by RP-HPLC

Sources & evidence

ORD record
ord-2f4fb0e8e9c44cc1a0fb4e7052a9ee68
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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