2-Chloropyrimidine → HCID 57420158, compound

HRID 1619218Notes

Reaction equation

HRID 1619218 reaction equation
Cl.[CH:2]12[NH:9][CH:6]([CH2:7][CH2:8]1)[CH2:5][C:4](=[O:10])[CH2:3]2.Cl[C:12]1[N:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C([O-])(O)=O.[Na+]>C(O)(C)C>[N:13]1[CH:14]=[CH:15][CH:16]=[N:17][C:12]=1[N:9]1[CH:6]2[CH2:7][CH2:8][CH:2]1[CH2:3][C:4](=[O:10])[CH2:5]2

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 516892Sodium BicarbonateHCID 130912188-Azabicyclo[3.2.1]octan-3-one hydrochloride

Product 1

HCID 57420158HCID 57420158, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 8-aza-bicyclo[3.2.1]octan-3-one hydrochloric acid (5.0 g, 30.9 mmol), 2-chloro-pyrimidine (4.95 g, 43.2 mmol), NaHCO3(7.78 g, 92.7 mmol) and isopropanol (200 ml) was maintained at reflux over weekend. The resulting reaction mixture was concentrated and purified by ISCO to afford 8-pyrimidin-2-yl-8-aza-bicyclo[3.2.1]octan-3-one (4.0 g, 52.9%) as a white solid: MS (M+1)=204. 1H NMR (MeOH) 8.36 (d, J=12 Hz 2H), 6.75 (m, 1H), 4.97 (m, 2H), 2.75 (d, J=12 Hz, 1H), 2.71 (d, J=12 Hz, 1H), 2.32 (d, J=50 Hz, 2H), 2.22 (m, 2H), 1.87 (m, 2H).

Workup

  1. temperatureat reflux over weekend
  2. customThe resulting reaction mixture
  3. concentrationwas concentrated
  4. custompurified by ISCO

Sources & evidence

ORD record
ord-d25a4282cb484ebdb7b1a7dc4aef0e2c
Source dataset
uspto-grants-2014_07
Patent number
US08772291B2

Reaction notes

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