Pyridine → 5-tert-butyl-3-[(2-chlorophenyl)methyl]-4H-triazolo[4,5-d]pyrimidin-7-one

HRID 2173501Notes

Reaction equation

HRID 2173501 reaction equation
NC1N(CC2C=CC=CC=2Cl)N=NC=1C(N)=O.N1C=CC=CC=1.C(Cl)(=O)C(C)(C)C.[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][N:39]1[C:43]([NH:44][C:45](=O)[C:46]([CH3:49])([CH3:48])[CH3:47])=[C:42]([C:51]([NH2:53])=[O:52])[N:41]=[N:40]1>CN(C)C(=O)C.O>[C:46]([C:45]1[NH:44][C:43]2[N:39]([CH2:38][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[Cl:31])[N:40]=[N:41][C:42]=2[C:51](=[O:52])[N:53]=1)([CH3:49])([CH3:48])[CH3:47]

Participants

7

Reactant 4

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 28153125-amino-1-[(2-chlorophenyl)methyl]-1H-1,2,3-triazole-4-carboxamideHCID 866832871-[(2-Chlorophenyl)methyl]-5-(2,2-dimethylpropanoylamino)triazole-4-carboxamide

Product 1

HCID 1784418645-tert-butyl-3-[(2-chlorophenyl)methyl]-4H-triazolo[4,5-d]pyrimidin-7-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
155 °C

Procedure

5-amino-1-(2-chlorobenzyl)-1H-1,2,3-triazole-4-carboxamide (10.80 g, 42.9 mmol, Eq: 1.00) was suspended in N,N-dimethylacetamide (50.2 g, 54.0 ml). Pyridine (5.1 g, 5.19 ml, 64.4 mmol, Eq: 1.5) was added followed by pivaloyl chloride (7.84 g, 8.00 ml, 64.4 mmol, Eq: 1.5) and the reaction mixture was heated to ca 80° C. After 3 h reaction (and complete conversion of the starting material to the intermediate), KHCO3 (21.6 g, 215 mmol, Eq: 5.00) was added and the suspension was heated to Tj=155° C. for 24 h to convert the 1-[(2-chlorophenyl)methyl]-5-(2,2-dimethylpropanoylamino)triazole-4-carboxamide intermediate to the product. The reaction mixture was cooled to RT and water (254 g, 254 ml) was added dropwise over 30 min. The brown suspension was cooled to 0° C., stirred for 1 h30 min and was filtered. The filter cake was washed with water (43.2 g, 43.2 ml) and dried at 500° C./5 mbar to give 11 g of the title compound as an off-white powder. MS(m/e): 318.0 (MH+).

Workup

  1. temperaturethe reaction mixture was heated to ca 80° C
  2. additionwas added
  3. temperatureThe reaction mixture was cooled to RT
  4. temperatureThe brown suspension was cooled to 0° C.
  5. filtrationwas filtered
  6. washThe filter cake was washed with water (43.2 g, 43.2 ml)
  7. customdried at 500° C./5 mbar

Sources & evidence

ORD record
ord-38752f38856f42ef812cd2a66317c2cd
Source dataset
uspto-grants-2015_06
Patent number
US09056866B2

Reaction notes

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