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

HRID 2389817Notes

Reaction equation

HRID 2389817 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13](O)[N:12]2[N:16]=[C:17]([CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:18]=[C:11]2[CH:10]=1.P(Cl)(Cl)([Cl:28])=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[Cl:28][C:13]1[N:12]2[N:16]=[C:17]([CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]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

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517484HCID 178517484, compound

Product 1

HCID 593131065-Chloro-7-(2,4-dichlorophenyl)-2-(morpholin-4-ylmethyl)[1,2,4]triazolo[1,5-c]pyrimidine

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
120 °C

Procedure

1250 mg (3.3 mmol) of 7-(2,4-dichlorophenyl)-2-(morpholin-4-ylmethyl)[1,2,4]triazolo-[1,5-c]pyrimidin-5-ol (Example 134A) are introduced into phosphoryl chloride (20 ml), 2.25 g (9.9 mmol) of benzyltriethylammonium chloride are added, and the reaction mixture is stirred at 120° C. for 12 h. The reaction mixture is slowly poured, while stirring vigorously, into saturated sodium bicarbonate solution (150 ml) and ice, and solid sodium bicarbonate (approx. 10 g) is added until a pH of 8 is reached. The solid is filtered off with suction and dried. 508 mg (39% of theory) of the product are obtained.

Workup

  1. additionare added
  2. additionThe reaction mixture is slowly poured
  3. additionis added until a pH of 8
  4. filtrationThe solid is filtered off with suction
  5. customdried
  6. custom508 mg (39% of theory) of the product are obtained

Sources & evidence

ORD record
ord-2123f54a98534e21a05beebb20e56324
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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