Sodium hydride → 2-Chloro-4-morpholin-4-yl-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidine

HRID 528450Notes

Reaction equation

HRID 528450 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([O:9][CH2:10][CH2:11][OH:12])=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:3]=1.[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[O:9][CH2:10][CH2:11][O:12][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 867117362-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethanol

Product 1

HCID 867117372-Chloro-4-morpholin-4-yl-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidineYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethanol (145 mg, 0.49 mmol) in THF (5 mL) was added sodium hydride (59 mg, 1.50 mmol, 60% dispersion in mineral oil) and the resulting mixture stirred at RT for 30 minutes. The reaction mixture was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo affording 2-Chloro-4-morpholin-4-yl-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidine as a white solid (114 mg, 90%). LCMS: RT=2.62 min, [M+H]+=258/260.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-672d7af1e47440eeacc488aafbe37c5e
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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