Sodium Carbonate → HCID 20682338, compound

HRID 861362Notes

Reaction equation

HRID 861362 reaction equation
[OH:1][CH2:2][C:3]1([CH3:12])[CH2:11][N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH:5]2[CH2:4]1.Cl[C:14]1[N:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[OH:1][CH2:2][C:3]1([CH3:12])[CH2:11][N:6]2[CH2:7][CH2:8][N:9]([C:14]3[N:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=3)[CH2:10][CH:5]2[CH2:4]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5834662-Chloro-5-fluoropyrimidineHCID 70199857HCID 70199857, compound

Product 1

HCID 20682338HCID 20682338, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (7RS,8aSR)-7-hydroxymethyl-7-methyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (1.08 g, 6.35 mmol), 0.925 g (6.98 mmol) of 2-chloro-5-fluoropyrimidine (Dunaiskis, A.; et al. Org. Prep. Proc. Int., 1995, 27, 600-602), and 1.48 g (13.96 mmol) of sodium carbonate and 65 mL of water was heated at 90° C. for 72 h. the solution was cooled and extracted with chloroform (3×). The combined organic layers were dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography eluting with chloroform:methanol (95:5) gave 0.80 g (47%) of the title compound. 13C NMR (CDCl3): a 25.5, 39.5, 41.7, 43.3, 48.7, 51.2, 62.3, 63.8, 71.0, 144.9, 145.2, 149.8, 153.1, 158.9. m/z (MH+) 267.

Workup

  1. temperaturewas cooled
  2. extractionextracted with chloroform (3×)
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash silica gel chromatography
  7. washeluting with chloroform:methanol (95:5)

Sources & evidence

ORD record
ord-2bb2b5b109bb4b1c9b1e04d802aec73e
Source dataset
uspto-grants-1998_02
Patent number
US05714487

Reaction notes

Loading…