Sodium Methoxide → 2-Amino-4-methoxy-6-(4,5-dihydrothiazol-2-yl-thiomethyl)pyrimidine

HRID 981746Notes

Reaction equation

HRID 981746 reaction equation
[SH:1][C:2]1[S:3][CH2:4][CH2:5][N:6]=1.C[O-].[Na+].[NH2:10][C:11]1[N:16]=[C:15]([CH2:17]Cl)[CH:14]=[C:13]([O:19][CH3:20])[N:12]=1>CO.O>[NH2:10][C:11]1[N:12]=[C:13]([O:19][CH3:20])[CH:14]=[C:15]([CH2:17][S:1][C:2]2[S:3][CH2:4][CH2:5][N:6]=2)[N:16]=1

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 138848154-(Chloromethyl)-6-methoxypyrimidin-2-amineHCID 178527880HCID 178527880, compound

Product 1

HCID 200708312-Amino-4-methoxy-6-(4,5-dihydrothiazol-2-yl-thiomethyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

11.9 g of 4,5-dihydro-2-mercapto-thiazole are suspended in 100 ml of methanol, and to the suspension are added 18.0 g of 30% methanolic sodium methylate solution. To the formed clear solution are subsequently added 17.4 g of 2-amino-4-chloromethyl-6-methoxy-pyrimidine, and refluxing is carried out for 1 hour. After the solution has cooled, it is diluted with about 1 liter of water, and the product which precipitates is separated and dried. The yield is 22.5 g (88% of theory) of 2-amino-4-methoxy-6-(4,5-dihydrothiazol-2-yl-thiomethyl)-pyrimidine, m.p. 122°-124° C.

Workup

  1. temperaturerefluxing
  2. temperatureAfter the solution has cooled
  3. customthe product which precipitates
  4. customis separated
  5. customdried

Sources & evidence

ORD record
ord-fe2f48cd34384511922bff0d32a36714
Source dataset
uspto-grants-1991_02
Patent number
US04992549

Reaction notes

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