Acetic Acid → HCID 178422936, compound

HRID 2278433Notes

Reaction equation

HRID 2278433 reaction equation
[CH3:1][CH:2]1[O:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[N:14]=[C:13]([O:15]C)[C:12]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[CH:18]=3)=[CH:11][N:10]=2)[CH2:3]1.C(O)(=O)C>Br.CO>[CH3:8][C@H:6]1[O:7][C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[NH:10][CH:11]=[C:12]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[CH:18]=3)[C:13](=[O:15])[N:14]=2)[CH2:5]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67513552HCID 67513552, compound

Product 1

HCID 178422936HCID 178422936, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

2,6-Dimethyl-4-[4-(methyloxy)-5-(2-methyl-4-pyridinyl)-2-pyrimidinyl]morpholine (1.42 g, 4.52 mmol) was dissolved in 33% hydrobromic acid in acetic acid (45.4 ml, 836 mmol) and heated at 80° C. for 18 hours. It was confirmed reaction had progressed to completion by LC/MS. The reaction mixture was allowed to cool to room temperature. The product was then diluted with methanol and passed down a 50 g SCX column. The impurities were eluted with methanol, followed by elution of the product with 2M ammonia/methanol. The fractions containing product were combined and evaporated under reduced pressure to give the title compound as a white solid (760 mg, 2.53 mmol, 56.0 yield). LC/MS [M+H]+=301.

Workup

  1. customreaction
  2. temperatureto cool to room temperature
  3. washThe impurities were eluted with methanol
  4. washfollowed by elution of the product with 2M ammonia/methanol
  5. additionThe fractions containing product
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-21b174e0c4b54f689042357f596486bf
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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