Sodium hydride → HCID 118036789, compound

HRID 1777951Notes

Reaction equation

HRID 1777951 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([OH:6])[CH3:5].[Cl:7][C:8]1[N:13]=[C:12](Cl)[C:11]([Cl:15])=[CH:10][N:9]=1.[H-].[Na+]>C1COCC1>[Cl:7][C:8]1[N:13]=[C:12]([O:6][C@@H:4]([CH3:5])[CH2:3][O:2][CH3:1])[C:11]([Cl:15])=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2372592,4,5-TrichloropyrimidineHCID 6993459(2S)-1-methoxypropan-2-ol

Product 1

HCID 118036789HCID 118036789, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-1-Methoxypropan-2-ol (0.58 ml, 5.88 mmol) was added drop wise to a mixture of 2,4,5-trichloropyrimidine (0.63 ml, 5.34 mmol) and NaH (60% dispersion in mineral oil, 0.24 g, 5.88 mmol) in THF (10 ml) at room temperature. After 30 minutes the reaction mixture was partitioned between water and DCM, the organic layer washed with water, dried over Na2SO4 and evaporated to give the title compound as a yellow-brown oil. (UPLC-MS 7) tR 1.01; ESI-MS 237.0 and 238.9 [M+H]+.

Workup

  1. customAfter 30 minutes the reaction mixture was partitioned between water and DCM
  2. washthe organic layer washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-cc31da7c56ae406b9e9f819cf258b50b
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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