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

HRID 1352705Notes

Reaction equation

HRID 1352705 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:12][N:7]2[CH2:8][CH2:9][NH:10][CH2:11][C@@H:6]2[CH2:5][CH2:4]1.Cl[C:14]1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[OH:1][CH2:2][C@H:3]1[CH2:12][N:7]2[CH2:8][CH2:9][N:10]([C:14]3[N:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH2:11][C@@H:6]2[CH2:5][CH2:4]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)-methanolYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2.52 g (14.8 mmol) of (7R,9aS)-7-hydroxymethyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (Preparation 1), 1.70 g (14.8 mmol) of 2-chloropyrimidine and 6.91 g (65.2. mmol) of sodium carbonate in 150 mL of water was heated at 90° C. for 16 h.; then cooled and extracted with chloroform (3×). The organic layer was dried (magnesium sulfate), filtered and evaporated to give 3.25 g (89%) of the title compound which was used without purification in subsequent reactions.

Workup

  1. temperaturethen cooled
  2. extractionextracted with chloroform (3×)
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ea6b85eee8a14edea06bfde8bd6b2995
Source dataset
uspto-grants-2007_05
Patent number
US07220753B2

Reaction notes

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