Sodium hydride → HCID 69431554, compound

HRID 515911Notes

Reaction equation

HRID 515911 reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][OH:11])[CH2:5][CH2:4]1.[Br:12][C:13]1[CH:14]=[N:15][C:16](Cl)=[N:17][CH:18]=1.[Cl-].[NH4+].C([O-])(O)=O.[Na+]>O1CCCC1.O>[Br:12][C:13]1[CH:14]=[N:15][C:16]([O:11][CH2:10][CH2:9][N:6]2[CH2:7][CH2:8][O:3][CH2:4][CH2:5]2)=[N:17][CH:18]=1

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 611632-MorpholinoethanolHCID 516892Sodium BicarbonateHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 69431554HCID 69431554, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

NaH (1.0 g, 25.0 mmol, 60% in oil) suspended in anhydrous tetrahydrofuran is cooled at 0° C. in an ice bath under argon, and then 2-morpholinoethanol (2.7 g, 20.7 mmol) is added dropwise. The ice bath is withdrawn and the suspension is stirred for 1 hour at ambient temperature. 5-Bromo-2-chloro-pyrimidine (4.0 g, 20.7 mmol) is then added at ambient temperature and the reaction mixture is stirred for 16 hours at ambient temperature. Saturated aqueous ammonium chloride solution (10 mL) and water (10 mL) are added to the reaction mixture; the pH is adjusted to 9 by adding saturated aqueous NaHCO3 solution. The resulting solution is extracted 3 times with ethyl acetate, the organic phase is then washed with brine, dried over MgSO4, and then evaporated to dryness. The expected compound precipitates out by means of the addition of petroleum ether.

Workup

  1. customThe ice bath is withdrawn
  2. stirringthe reaction mixture is stirred for 16 hours at ambient temperature
  3. extractionThe resulting solution is extracted 3 times with ethyl acetate
  4. washthe organic phase is then washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customThe expected compound precipitates out by means of the addition of petroleum ether

Sources & evidence

ORD record
ord-b6f751933534466e9fc9a3b057c65513
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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