1H-1,2,4-Triazole → N-(4-fluorobenzyl)-6-(4-fluorophenyl)-4-(1H-1,2,4-triazol-1-yl)pyrido[3,2-d]pyrimidin-2-amine

HRID 1025527Notes

Reaction equation

HRID 1025527 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]2[N:9]=[C:10](O)[C:11]3[N:17]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[NH:28]1[CH:32]=[N:31][CH:30]=[N:29]1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)Cl>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]2[N:9]=[C:10]([N:28]3[CH:32]=[N:31][CH:30]=[N:29]3)[C:11]3[N:17]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178518098HCID 178518098, compound

Product 1

HCID 69319686N-(4-fluorobenzyl)-6-(4-fluorophenyl)-4-(1H-1,2,4-triazol-1-yl)pyrido[3,2-d]pyrimidin-2-amineYield 92.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4-fluorobenzylamino)-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-4-ol (2 g), 1,2,4-triazole (1.52 g), DIEA (3.55 g) and POCl3 (3.4 g) in acetonitrile (20 mL) was stirred at room temperature for 1 hour. Ethyl acetate was added to the mixture, which was then washed twice with brine. The organic layer was dried and concentrated to provide 2.1 g of N-(4-fluorobenzyl)-6-(4-fluorophenyl)-4-(1H-1,2,4-triazol-1-yl)pyrido[3,2-d]pyrimidin-2-amine which was characterized by its mass spectrum as follows: MS (m/z) 416 [M+H]+.

Workup

  1. washwas then washed twice with brine
  2. customThe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-05efa3c6d7af451293aa3c715261f6f4
Source dataset
uspto-grants-2014_05
Patent number
US08729089B2

Reaction notes

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