1H-1,2,4-Triazole → HCID 178508321, compound

HRID 474373Notes

Reaction equation

HRID 474373 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=O)[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.C(N(CC)C(C)C)(C)C.[NH:29]1[CH:33]=[N:32][CH:31]=[N:30]1.P(Cl)(Cl)(Cl)=O>C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([C:33]2[N:32]=[CH:31][NH:30][N:29]=2)[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 92571H-1,2,4-Triazole2×HCID 24813Phosphorus oxychloride2×HCID 81531Diisopropylethylamine2×HCID 1361375922-Amino-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-4(1H)-one

Product 1

HCID 178508321HCID 178508321, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

To a stirred suspension of 2-amino-6-(4-fluorophenyl)-3H-pyrido[3,2-d]pyrimidin-4-one (2.56 g, 10 mmole) and N,N-diisopropylethylamine (3.5 mL, 20 mmol) in acetonitrile (75 mL) was added a suspension of 1,2,4-triazole (1.38 g, 20 mmol) and phosphorus oxychloride (1.8 mL, 20 mmol) in dry acetonitrile (75 mL), portion-wise. The reaction mixture was stirred at ambient temperature for 20 hours. Then to it was added N,N-diisopropylethylamine (3.5 mL, 20 mmol), followed by a suspension of 1,2,4-triazole (1.38 g, 20 mmol) and phosphorus oxychloride (1.8 mL, 20 mmol) in dry acetonitrile (50 mL). The reaction mixture was stirred for 3 days until all the starting material was consumed. The solid was collected by vacuum filtration, washed with small amounts of acetonitrile, dichloromethane and diethyl ether, and then dried under high vacuum for one day to afford 3.18 g of the title compound as a light yellow solid. which was characterized by its mass spectrum as follows: MS (m/z): 308.1 ([M+H]+, 100).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 3 days until all the starting material
  3. customwas consumed
  4. filtrationThe solid was collected by vacuum filtration
  5. washwashed with small amounts of acetonitrile, dichloromethane and diethyl ether
  6. customdried under high vacuum for one day

Sources & evidence

ORD record
ord-8efff2075d8044d3b0c6a8751778e33d
Source dataset
uspto-grants-2014_01
Patent number
US08637531B2

Reaction notes

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