Sodium Carbonate → HCID 54484575, compound

HRID 1977064Notes

Reaction equation

HRID 1977064 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][C:17]([F:20])=[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][C:17]([F:20])=[CH:16][N:15]=3)[CH2:11][C@@H:6]2[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5834662-Chloro-5-fluoropyrimidineHCID 9855588(Octahydro-2H-pyrido[1,2-a]pyrazin-7-yl)methanol

Product 1

HCID 54484575HCID 54484575, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.31 g (13.6 mmol) of (7S,9aS)-7-hydroxymethyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (Preparation 2), 1.98 g (15.0 mmol) of 2-chloro-5-fluoropyrimidine (B. Baasner, E. Klauke, J. Fluorine Chem., 1989, 45, 417), 4.32 g (40.8 mmol) of sodium carbonate and 50 mL of water was heated at reflux for 16 h. The mixture was cooled to room temperature and extracted with chloroform (3×). The combined organic layers were dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography with 95:5 chloroform:methanol gave 2.7 g (75%) of the title compound. mp (base) 111-112° C. 13C NMR (base, CDCl3): δ26.5, 27.3, 34.2, 44.3, 49.8, 54.8, 58.8, 60.7, 68.2, 145.0, 145.3, 149.9, 153.2, 158.6. HRMS calcd for C13H19FN4O: 266.1543, found: 266.1530.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. extractionextracted with chloroform (3×)
  4. dry with materialThe combined organic layers were dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash silica gel chromatography with 95:5 chloroform

Sources & evidence

ORD record
ord-ce4087563ff442eb9a3d8949bc806daf
Source dataset
uspto-grants-2001_05
Patent number
US06231833B1

Reaction notes

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