2-Methyl-2-thiopseudourea sulfate → HCID 11740630, compound

HRID 1708413Notes

Reaction equation

HRID 1708413 reaction equation
[CH2:1]([C:4]1[N:9]=[C:8]([CH3:10])[N:7]=[C:6]([NH:11]N)[C:5]=1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]#[N:27])=[CH:16][CH:15]=1)[CH2:2][CH3:3].S(O)(O)(=O)=O.CS[C:35](=[NH:37])[NH2:36]>O>[CH2:1]([C:4]1[N:9]=[C:8]([CH3:10])[N:7]2[N:36]=[C:35]([NH2:37])[N:11]=[C:6]2[C:5]=1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]#[N:27])=[CH:16][CH:15]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 752702-Methyl-2-thiopseudourea sulfateHCID 10473537HCID 10473537, compound

Product 1

HCID 11740630HCID 11740630, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 g of 6-n-propyl-2-methyl-4-hydrazino-5-[(2'-cyano-4-biphenylyl)methyl]pyrimidine, prepared in Example 12, and 5 g of 2-methyl-2-thiopseudourea sulphate are heated to reflux for 16 hours. After the addition of water, the crystals formed are drained and washed with ether and then with ethyl acetate before taken up in dilute sodium hydroxide solution and extracted with chloroform. The organic phase is dried over magnesium sulphate and evaporated under vacuum, to give a residue which crystallises in a mixture of isopropyl ether and ethyl acetate to give 1.8 g of 7-n-propyl-5-methyl-2-amino-8-[(2 '-cyano-4-biphenylyl)methyl]-1,2,4-triazolo[1,5-c]pyrimidine in the form of crystals of melting point 150° C.

Workup

  1. temperatureare heated
  2. temperatureto reflux for 16 hours
  3. customthe crystals formed
  4. washwashed with ether
  5. extractionextracted with chloroform
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. customevaporated under vacuum
  8. customto give a residue which
  9. customcrystallises in a mixture of isopropyl ether and ethyl acetate

Sources & evidence

ORD record
ord-946599c307344fce8cd7e8172fbe0af8
Source dataset
uspto-grants-1994_10
Patent number
US05358950

Reaction notes

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