Acetic Acid → HCID 67248097, compound

HRID 410567

Reaction equation

HRID 410567 reaction equation
C(O)(=O)C.Cl[C:6]1[N:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:8][N:7]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[NH2:19]>O1CCOCC1>[Br:15][C:16]1[CH:17]=[C:18]([NH:19][C:6]2[N:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:8][N:7]=2)[CH:20]=[C:21]([CH3:23])[CH:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 30185263-Bromo-5-methylanilineHCID 249019162-Chloro-4-isopropylpyrimidine

Product 1

HCID 67248097HCID 67248097, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Acetic acid (0.192 mL, 3.35 mmol) was added to commercially available 2-chloro-4-(propan-2-yl)pyrimidine (0.5 g, 3.19 mmol) and 3-bromo-5-methylaniline (0.900 g, 3.19 mmol) suspended in dioxane (6.39 mL). Reaction was heated to 120° C. (bath temp) overnight. Then, the reaction was cooled to room temperature and purified by column chromatography on silica gel eluting with ethyl acetate and hexanes to give N-(3-bromo-5-methylphenyl)-4-(propan-2-yl)-pyrimidin-2-amine (959.8 mg, 3.13 mmol, 98%) as a white solid.

Workup

  1. customReaction
  2. temperatureThen, the reaction was cooled to room temperature
  3. custompurified by column chromatography on silica gel eluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-6f0a6f8c243e448aacaf35fdaef543d9
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Linked notes

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