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

HRID 528460Notes

Reaction equation

HRID 528460 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([O:9][CH2:10][CH:11]([OH:13])[CH3:12])=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:3]=1.[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[O:9][CH2:10][CH:11]([CH3:12])[O:13][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 867117451-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-ol

Product 1

HCID 867117462-Chloro-7-methyl-4-morpholin-4-yl-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-ol (148 mg, 0.48 mmol) in THF (8 mL) was added sodium hydride (58 mg, 1.44 mmol, 60% dispersion in mineral oil) and the resulting mixture stirred at RT for 4 hours. 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-7-methyl-4-morpholin-4-yl-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidine as an off-white solid (139 mg, quantitative). LCMS: RT=2.94 min, [M+H]+=272/274.

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-7640e62d3bf84a7e96697f5203f7527d
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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