Sodium Carbonate → cis-(2-Pyrimidin-2-yl-octahydro-pyrido[1,2-a]pyrazin-7-yl)-methanol

HRID 1172560Notes

Reaction equation

HRID 1172560 reaction equation
[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[CH2:7][C@H:8]([CH2:11][OH:12])[CH2:9][CH2:10][C@@H:2]12.Cl[C:14]1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[Na+].[Na+]>O>[N:15]1[CH:16]=[CH:17][CH:18]=[N:19][C:14]=1[N:6]1[CH2:5][CH2:4][N:3]2[CH2:7][C@H:8]([CH2:11][OH:12])[CH2:9][CH2:10][C@H:2]2[CH2:1]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 744042-ChloropyrimidineHCID 10035034((7R,9AS)-Octahydro-1H-pyrido[1,2-A]pyrazin-7-YL)methanol

Product 1

HCID 14995231cis-(2-Pyrimidin-2-yl-octahydro-pyrido[1,2-a]pyrazin-7-yl)-methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

Cis-(octahydro-pyrido[1,2-a]pyrazin-7-yl)-methanol (1 eq), 2-chloro-pyrimidine (1 eq.), and Na2CO3 (1 eq.) were dissolved in water. The mixture was stirred at around 95° C. for overnight. The solution was cooled to room temperature and extracted with methylene chloride. The combined organic layers was washed with brine, dried over Na2SO4, filtered and concentrated to give cis-(2-pyrimidin-2-yl-octahydro-pyrido[1,2-a]pyrazin-7-yl)-methanol as a white solid. This material was used in the next step without further purification.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3f01ef0aa3e34a8da279058e905b7167
Source dataset
uspto-grants-2010_11
Patent number
US07834014B2

Reaction notes

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