Sodium Carbonate → HCID 15817415, compound

HRID 1352695Notes

Reaction equation

HRID 1352695 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C@H:12]1[CH2:21][N:16]3[CH2:17][CH2:18][NH:19][CH2:20][C@@H:15]3[CH2:14][CH2:13]1)[CH:6]=[CH:5]2.Cl[C:23]1[N:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C@H:12]1[CH2:21][N:16]3[CH2:17][CH2:18][N:19]([C:23]4[N:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=4)[CH2:20][C@@H:15]3[CH2:14][CH2:13]1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5834662-Chloro-5-fluoropyrimidineHCID 53779442HCID 53779442, compound

Product 1

HCID 15817415HCID 15817415, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2.20 g (7.67 mmol) of (7R,9aS)-7-(5-fluoroindol-1-yl)methyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine, 1.02 g (7.67 mmol) of 2-chloro-5-fluoropyrimidine and 1.95 g (18.4 mmol) of sodium carbonate in 100 mL of water was stirred at 95° C. for 72 h. The mixture was cooled to room temperature, extracted with chloroform (3×), the combined organic phase was washed with brine, dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography with 50:50 ethyl acetate:hexane gave 1.17 g (40%) of the title compound. mp (.HCl) 180–182° C. HRMS calc for HRMS calcd for C21H23F2N5: 383.1922, found: 383.1924.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with chloroform (3×)
  3. washthe combined organic phase was washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash silica gel chromatography with 50:50 ethyl acetate

Sources & evidence

ORD record
ord-87b729b992b045fbacf56ff20af8c91a
Source dataset
uspto-grants-2007_05
Patent number
US07220753B2

Reaction notes

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