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

HRID 528493Notes

Reaction equation

HRID 528493 reaction equation
[CH:1]1([CH:4]([OH:21])[CH2:5][O:6][C:7]2[C:8](Cl)=[N:9][C:10]([Cl:19])=[N:11][C:12]=2[N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH2:3][CH2:2]1.[H-].[Na+]>C1COCC1>[Cl:19][C:10]1[N:11]=[C:12]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:7]2[O:6][CH2:5][CH:4]([CH:1]3[CH2:3][CH2:2]3)[O:21][C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 867117671-Cyclopropyl-2-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethanol

Product 1

HCID 867117542-Chloro-7-cyclopropyl-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-cyclopropyl-2-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethanol (196 mg, 0.59 mmol) in THF (10 mL) was added sodium hydride (65 mg, 1.77 mmol, 65% dispersion in mineral oil) and the reaction mixture stirred at RT for 4 hours. The reaction was quenched with saturated aqueous ammonium chloride solution (15 mL) then extracted with ethyl acetate (3×20 mL). The combined organic phases were dried (Na2SO4) and concentrated in vacuo giving 2-Chloro-7-cyclopropyl-4-morpholin-4-yl-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidine as a white solid (205 mg, quantitative). LCMS: RT=3.19 min, [M+H]+=298/300.

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride solution (15 mL)
  2. extractionthen extracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7895a64a311f4b50b0e9ee321fc50f33
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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