Hydrogen Bromide → HCID 59749166, compound

HRID 747162Notes

Reaction equation

HRID 747162 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([NH2:14])[N:11]=[C:10]([NH2:15])[C:9]=2[C:16]2[CH:17]=[N:18][C:19]([O:22]C)=[CH:20][CH:21]=2)[CH:5]=[CH:6][CH:7]=1.Br.[OH-].[Na+]>C(O)(=O)C>[NH2:14][C:12]1[N:11]=[C:10]([NH2:15])[C:9]([C:16]2[CH:21]=[CH:20][C:19](=[O:22])[NH:18][CH:17]=2)=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[N:13]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 23020399HCID 23020399, compound

Product 1

HCID 59749166HCID 59749166, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6-(3-fluorophenyl)-5-(6-methoxy-3-pyridyl)-2,4-pyrimidinediamine (5.00 g, 16.1 mmol) in acetic acid (30 ml)/concentrated hydrobromic acid (50 ml) was stirred at 100° C. for 1.5 hours. After cooling as it was, the reaction mixture was adjusted to pH 12 to 13 with 5N sodium hydroxide and washed with ethylacetate. The aqueous layer was neutralized with 5N hydrochloric acid. The resulting solid was collected by filtration, to give the title compound (3.36 g, 70%) as a colorless solid.

Workup

  1. temperatureAfter cooling as it
  2. washwashed with ethylacetate
  3. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-6341960da5a54aa69c898fbfa7bafc10
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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