Dimethyl Sulfoxide → HCID 14011772, compound

HRID 986219Notes

Reaction equation

HRID 986219 reaction equation
[OH-].[K+].CS(C)=O.[CH3:7][N:8]([CH3:17])[C:9]1[N:14]=[C:13]([CH3:15])[C:12]([OH:16])=[CH:11][N:10]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[CH3:17][N:8]([CH3:7])[C:9]1[N:14]=[C:13]([CH3:15])[C:12]([O:16][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 131707422-(Dimethylamino)-4-methylpyrimidin-5-ol

Product 1

HCID 14011772HCID 14011772, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium hydroxide (85%, 2.64 g, 40 mmol) was powdered and added to 20 ml of DMSO at room temperature. 2-Dimethylamino-4-methyl-5-hydroxypyrimidine (1.53 g, 10 mmol) was added and the reaction mixture stirred for 5 minutes at room temperature. Benzylbromide (1.2 ml, 10 mmol) was added and the reaction mixture after stirring for a half hour at room temperature was poured into 50 ml of water. The reaction mixture was extracted four times with 50 ml hexane portions. The combined hexane extracts were dried over Na2SO4, filtered, and evaporated. Recrystallization of the formed solid from hexane yielded 1.8 g (75% yield) of the title compound as pale yellow crystals, m.p. 73° to 74° C.

Workup

  1. stirringthe reaction mixture after stirring for a half hour at room temperature
  2. extractionThe reaction mixture was extracted four times with 50 ml hexane portions
  3. dry with materialThe combined hexane extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customRecrystallization of the formed solid from hexane

Sources & evidence

ORD record
ord-7702377ff76b4733b32978ae35784125
Source dataset
uspto-grants-1987_12
Patent number
US04711888

Reaction notes

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