Dimethylformamide → HCID 21241599, compound

HRID 1761483Notes

Reaction equation

HRID 1761483 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]=[C:9]([SH:11])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:12]N(C)C=O.[H-].[Na+].IC>O>[CH3:12][S:11][C:9]1[S:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=2[N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178508728HCID 178508728, compound

Product 1

HCID 21241599HCID 21241599, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled (below 25° C.) mixture of 13.9 parts of 7-aminothiazolo[5,4-d]pyrimidin-2-thiol and 180 parts of N,N-dimethylformamide were added portionwise 4.3 parts of a sodium hydride dispersion 50% while cooling. After stirring for 1 hour, 11.5 parts of iodomethane were added dropwise at a temperature below 25° C. Upon completion, stirring was continued for 4 hours at room temperature. The reaction mixture was poured into water. The product was filtered off (the filtrate was set aside) and dried, yielding a first fraction of 5.9 parts of 2-(methylthio)thiazolo[5,4-d]pyrimidin-7-amine (intermediate 46). From the filtrate, the aqueous layer was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was stirred in 2,2'-oxybispropane. The product was filtered off and dried, yielding fraction of 3.9 parts of 2-(methylthio)thiazolo[5,4-d]pyrimidin-7-amine (intermediate 46). Total yield: 9.8 parts (65.6%) of 2 -(methylthio)thiazolo[5,4-d]pyrimidin-7-amine (intermediate 46).

Workup

  1. temperaturecooled
  2. temperaturewhile cooling
  3. stirringAfter stirring for 1 hour
  4. stirringUpon completion, stirring
  5. filtrationThe product was filtered off (the filtrate
  6. customdried

Sources & evidence

ORD record
ord-71187968244642a990481f3dd97f0b15
Source dataset
uspto-grants-1989_05
Patent number
US04826848

Reaction notes

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