Dimethyl Sulfate → HCID 20158316, compound

HRID 986218Notes

Reaction equation

HRID 986218 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20]C=CC=2)[N:3]=1.[H-].[Na+].[CH3:24]OS(OC)(=O)=O.[CH2:31]1[CH2:35]OC[CH2:32]1>>[CH3:9][C:6]1[C:7]([O:8][CH3:24])=[C:2]([CH3:1])[N:3]=[C:4]([NH:10][CH2:11][CH:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:21][CH:20]=2)[CH2:32][CH2:31][CH3:35])[N:5]=1

Participants

5

Reactant 4

HCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 14011782HCID 14011782, compound

Product 1

HCID 20158316HCID 20158316, compound

Conditions

Temperature
0 °C

Procedure

4,6-Dimethyl-5-hydroxy-2-phenpentylaminopyrimidine (0.5 g, 1.8 mmol) prepared by the method of example 1 was dissovled in dry THF (20 ml) under nitrogen and treated with sodium hydride (0.07 g, 1.8 mmol, 60% oil dispersion). The reaction mixture was stirred at 0° C. for 2 hours. Dimethylsulfate (0.11 ml, 1.8 mmol) was added with a syringe and the reaction was stirred for an additional hour. After quenching with saturated NH4Cl (aqueous, 20 ml), the reaction mixture was extracted with ethylacetate (75 ml). The extracts were washed with 50 ml water and 50 ml brine, dried over MgSO4 and concentrated. Chromatography on silica gel with ethylacetate/hexane (1:1) eluent yielded 0.15 g of the title compound as a yellow oil, m.p.: 31° to 33° C.

Workup

  1. stirringthe reaction was stirred for an additional hour
  2. customAfter quenching with saturated NH4Cl (aqueous, 20 ml)
  3. extractionthe reaction mixture was extracted with ethylacetate (75 ml)
  4. washThe extracts were washed with 50 ml water and 50 ml brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6d0a7362a81a4c54bf2315305fd02ba9
Source dataset
uspto-grants-1987_12
Patent number
US04711888

Reaction notes

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