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Phosphorus oxychloride → 5-Chloro-7-(2,4-dichlorophenyl)-2-(1-methylpiperidin-4-yl)[1,2,4]triazolo[1,5-c]pyrimidine

HRID 2088682
Notes
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Reaction equation

HRID 2088682 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:14][C:13](=O)[N:12]2[N:16]=[C:17]([CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[N:18]=[C:11]2[CH:10]=1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:33])=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:33][C:13]1[N:12]2[N:16]=[C:17]([CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[N:18]=[C:11]2[CH:10]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[N:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium Bicarbonate2×HCID 1361041907-(2,4-Dichlorophenyl)-2-(1-methylpiperidin-4-yl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

Product 1

HCID 583059825-Chloro-7-(2,4-dichlorophenyl)-2-(1-methylpiperidin-4-yl)[1,2,4]triazolo[1,5-c]pyrimidine

Reagents, catalysts & solvents 1

HCID 66133
Benzyl triethylammonium chloride
Catalyst

Conditions

Temperature
120 °C

Procedure

270 mg (0.71 mmol) of 7-(2,4-dichlorophenyl)-2-(1-methylpiperidin-4-yl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 48A) were initially charged in phosphorus oxychloride (2 ml), 650 mg (2.90 mmol) of benzyltriethylammonium chloride were added and the mixture was then stirred at 120° C. for 3 h. The reaction mixture was poured into saturated aqueous sodium bicarbonate solution (150 ml), and solid sodium bicarbonate was added until a pH of 7 had been reached. The solid was filtered off with suction and dried. This gave 190 mg (65% of theory) of the product as a solid.

Workup

  1. additionwas added until a pH of 7
  2. filtrationThe solid was filtered off with suction
  3. customdried

Sources & evidence

ORD record
ord-b12c89ef2cba4cfb8a99278e78fca926
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08436003B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes