Methanol → HCID 57566529, compound

HRID 1929597Notes

Reaction equation

HRID 1929597 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([C:15]2[N:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:3]=1.[N+:21]([O-])([OH:23])=[O:22].CO>C(O)(C(F)(F)F)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([C:15]2[N:16]=[CH:17][CH:18]=[CH:19][N:20]=2)[C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:12])([CH3:13])[CH3:11])=[C:6]([N+:21]([O-:23])=[O:22])[CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 944Nitric AcidHCID 57566634HCID 57566634, compound

Product 1

HCID 57566529HCID 57566529, compoundYield 5,400.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a 5° C. suspension of N-(4-bromo-2-pyrimidin-2-yl-phenyl)-2,2-dimethyl-propionamide (32.6 grams, 97.5 mmoles) in TFA (400 mL) was added 90% nitric acid (70 mL, 1.46 mmoles) over a 30 minute period. The mixture was then allowed to warm to room temperature and stir for a total of 2 hours. The crude reaction (now homogenous) was poured into ice producing a pasty mass. The mixture was diluted to 2 L total volume with water, treated with 500 mL of methanol, and vigorously stirred for 12 hours. The resulting solids were filtered, washed with copious amounts of water, then vacuum dried at 50° C. to afford the title compound (29.9 grams, 81% yield) as a tan powder.

Workup

  1. customThe crude reaction (now homogenous)
  2. additionwas poured into ice producing a pasty mass
  3. stirringvigorously stirred for 12 hours
  4. filtrationThe resulting solids were filtered
  5. washwashed with copious amounts of water
  6. customvacuum dried at 50° C.

Sources & evidence

ORD record
ord-0057045071e64c51bf390814960d6850
Source dataset
uspto-grants-2012_05
Patent number
US08188095B2

Reaction notes

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