Water → HCID 86725452, compound

HRID 1050937Notes

Reaction equation

HRID 1050937 reaction equation
[C:1]([C:5]1[N:10]=[C:9](O)[CH:8]=[C:7]([CH2:12][CH2:13][O:14][CH3:15])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O=P(Cl)(Cl)[Cl:18].O>C1(C)C=CC=CC=1.CN(C=O)C>[C:1]([C:5]1[N:10]=[C:9]([Cl:18])[CH:8]=[C:7]([CH2:12][CH2:13][O:14][CH3:15])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 178494793HCID 178494793, compound

Product 1

HCID 86725452HCID 86725452, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-tert-butyl-6-(2-methoxy-ethyl)-pyrimidin-4-ol (20 g, 95 mmol) in toluene (200 mL) and DMF (2 mL) was added dropwise POCl3 (36.5 g, 238 mmol) in an ice bath. The mixture was stirred for 3 hrs at room temperature. The reaction mixture was poured into water, extracted with DCM (400 mL×3). The organic layer was dried over Na2SO4 and concentrated to give the title compound (20 g, 92% yield) as a yellow oil.

Workup

  1. extractionextracted with DCM (400 mL×3)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-737f2114c4474d1d811a5835a2c7a9a5
Source dataset
uspto-grants-2016_07
Patent number
US09388141B2

Reaction notes

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