Sodium Carbonate → HCID 54484576, compound

HRID 1352706Notes

Reaction equation

HRID 1352706 reaction equation
Cl.Cl.[OH:3][CH2:4][C@H:5]1[CH2:14][N:9]2[CH2:10][CH2:11][NH:12][CH2:13][C@@H:8]2[CH2:7][CH2:6]1.Cl[C:16]1[N:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[OH:3][CH2:4][C@H:5]1[CH2:14][N:9]2[CH2:10][CH2:11][N:12]([C:16]3[N:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]=3)[CH2:13][C@@H:8]2[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5834662-Chloro-5-fluoropyrimidineHCID 22940604HCID 22940604, compound

Product 1

HCID 54484576HCID 54484576, compoundYield 114.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4.41 g (18.2 mmol) of (7R,9aS)-7-hydroxymethyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine dihyrochloride (Preparation 1), 3.78 g (28.5 mmol) of 2-chloro-5-fluoropyrimidine (B. Baasner, E. Klauke J. Fluroine Chem., 1989, 45, 417–430), and 9.07 g (85.6 mmol) of-sodium carbonate in 180 mL of water were heated at 95° C. for 16 h. The mixture was cooled to room temperature, extracted with chloroform (2×), dried (magnesium sulfate), filtered and evaporated. Purification by flash chromatography on silica gel using 95:5 chloroform:methanol gave 5.56 g (81%) of title compound. mp 148–149.5° C. 13C NMR (CDCl3): δ 26.8, 29.0, 39.1, 44.2, 49.7, 54.8, 58.7, 60.8, 66.2, 145.0, 145.3, 149.9, 153.2, 158.7. Anal calcd for C13H19FN4O: C, 58.63; H, 7.19; N, 21.04; found: C, 58.36; H, 7.18; N, 20.87

Workup

  1. extractionextracted with chloroform (2×)
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash chromatography on silica gel using 95:5 chloroform

Sources & evidence

ORD record
ord-f3c91a17d5ad48f9b78f51e7006802f2
Source dataset
uspto-grants-2007_05
Patent number
US07220753B2

Reaction notes

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