Hydrochloric Acid → HCID 18323817, compound

HRID 1251497Notes

Reaction equation

HRID 1251497 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH2:31][CH3:32])[C:12]1[N:17]=[C:16]([C:18]([N:20]2[CH2:25][CH2:24][C:23]3(OCC[O:26]3)[CH2:22][CH2:21]2)=[O:19])[CH:15]=[C:14]([CH3:30])[N:13]=1.Cl.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH2:31][CH3:32])[C:12]1[N:17]=[C:16]([C:18]([N:20]2[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]2)=[O:19])[CH:15]=[C:14]([CH3:30])[N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18689809HCID 18689809, compound

Product 1

HCID 18323817HCID 18323817, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution-of N-(2-bromo-4-(1-methylethyl)phenyl)-N-ethyl-4-((4,4-ethylenedioxypiperidino)carbonyl)-6-methylpyrimidinamine (260 mg) in a mixture of a 1N HCl solution (2.5 mL) and THF (2.5 mL) was stirred at reflux temperature for 20 h. The reaction mixture was poured into a 1N NaOH solution, and extracted three times with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the title product as a yellow oil (240 mg, 100% yield, Rf 0.75): NMR (CDCl3, 300 MHz): 7.5 (s, 1H), 7.2 (d, 1H, J=8), 7.1 (d, 1H, J=8), 6.8 (br s, 1H), 4.3-4.1 (m, 1H), 3.95-3.85 (m, 1H), 3.75-3.6 (m, 1H), 3.55-3.4 (m, 1H), 2.95-2.85 (m, 1H), 2.6-2.3 (m, 4H), 2.0-1.6 (m, 2H), 1.4-1.15 (m, 12H); CI-HRMS: Calcd (C22H27BrN4O2): 459.1396 (M+H); Found: 459.1386.

Workup

  1. temperatureat reflux temperature for 20 h
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a47736d5c23439eb896790072b2bfcd
Source dataset
uspto-grants-2002_01
Patent number
US06342503B1

Reaction notes

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