Diisopropylethylamine → [1,2,4]Triazolo[1,5-a]pyrimidin-2-amine, 5,7-dimethoxy-

HRID 411111Notes

Reaction equation

HRID 411111 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][C:12]([NH:14]C(=O)OCC)=S)[N:4]=1.Cl.NO.C([N:26](C(C)C)CC)(C)C>C(O)C>[NH2:26][C:12]1[N:11]=[C:5]2[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[N:6]2[N:14]=1

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 443297Hydroxyamine hydrochlorideHCID 13607520Ethyl [(4,6-dimethoxypyrimidin-2-yl)amino]carbono thioylcarbamate

Product 1

HCID 11194901[1,2,4]Triazolo[1,5-a]pyrimidin-2-amine, 5,7-dimethoxy-Yield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-[N′-(4,6-dimethoxypyrimidin-2-yl)-thiocarbamoyl]carbamate (0.50 g, 1.7 mmol) was mixed with ethanol (5 mL). To this mixture was added hydroxylamine hydrochloride (0.12 g, 1.7 mmol) and diisopropylethylamine (0.30 mL, 1.7 mmol). The resulting mixture was allowed to stir at room temperature. After 2.5 hours, additional diisopropylethylamine (0.30 mL, 1.7 mmol) was added to the mixture. After 48 hours the ethanol was removed in vacuo and the residue was partitioned between H2O and Et2O to give a powder. The powder was filtered and dried to afford the product as a tan powder (0.27 g, 82%). mp 215-220° C. 1H NMR (DMSO-d6): δ6.04 (s, 1H); 5.97 (bs, 2H); 4.04 (s, 3H).

Workup

  1. customAfter 48 hours the ethanol was removed in vacuo
  2. customthe residue was partitioned between H2O and Et2O
  3. customto give a powder
  4. filtrationThe powder was filtered
  5. customdried

Sources & evidence

ORD record
ord-44621870669b4cabbd9504acb69def24
Source dataset
uspto-grants-2003_05
Patent number
US06559101B2

Reaction notes

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