Ethanol → 5-(Phenylazo)-2-(4-pyridinyl)-4,6-pyrimidinediamine

HRID 2164329Notes

Reaction equation

HRID 2164329 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(O)C.C[O-].[Na+].[C:17]1([N:23]=[N:24][CH:25]([C:28]#[N:29])[C:26]#[N:27])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[C:17]1([N:23]=[N:24][C:25]2[C:26]([NH2:27])=[N:9][C:2]([C:3]3[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=3)=[N:10][C:28]=2[NH2:29])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 223472-(2-Phenyldiazenyl)propanedinitrileHCID 2776844Pyridine-4-amidine hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 133399325-(Phenylazo)-2-(4-pyridinyl)-4,6-pyrimidinediamineYield 61.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The intermediate 5-(phenylazo)-2-(4-pyridinyl)-4,6-pyrimidinediamine was prepared as follows: a mixture containing 477 g of isonicotinamidine hydrochloride, 3 liters of ethanol and 170 g of sodium methoxide was stirred for 30 minutes and to the mixture was added 340 g of α-(phenylazo)malononitrile and the reaction mixture was stirred under reflux for 5 hours and then poured into 3 liters of water. The solid that separated was collected, washed with water and dried in a vacuum oven at 90°-95° C. to yield 356 g of 5-(phenylazo)-2-(4-pyridinyl)-4,6-pyrimidinediamine, m.p. 302°-305° C.

Workup

  1. customThe intermediate 5-(phenylazo)-2-(4-pyridinyl)-4,6-pyrimidinediamine was prepared
  2. stirringthe reaction mixture was stirred
  3. temperatureunder reflux for 5 hours
  4. customThe solid that separated
  5. customwas collected
  6. washwashed with water
  7. customdried in a vacuum oven at 90°-95° C.

Sources & evidence

ORD record
ord-cb567f4dc2ca44c68784e81fb6388c9a
Source dataset
uspto-grants-1985_03
Patent number
US04503228

Reaction notes

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