Dimethylformamide → HCID 13208054, compound

HRID 905328Notes

Reaction equation

HRID 905328 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:3]=1[CH2:4][NH:5][C:6]1[C:11](C2C=CC=CC=2)=[C:10]([NH:18][CH3:19])[N:9]=[C:8](N=NC2N=CC=CN=2)[N:7]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C[N:42](C)C=O>[OH-].[Na+]>[NH2:42][C:11]1[C:6]([NH:5][CH2:4][C:3]2[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:2]=2[Cl:1])=[N:7][CH:8]=[N:9][C:10]=1[NH:18][CH3:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24489Sodium DithioniteHCID 70525814HCID 70525814, compound

Product 1

HCID 13208054HCID 13208054, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In N,N-dimethylformamide (20 ml) and 2 N NaOH (5 ml) was dissolved 4-(2-chloro-6-fluorobenzyl)amino-6-methylamino-5-phenylazopyrimidine (1.112 g, 3 mmols), and sodium dithionite (3.27 g, 15 mmol; purity 80%) was added portionwise to the solution with stirring at 140°-150° C. The mixture was stirred at the same temperature for 30 minutes, after which it was concentrated to dryness under reduced pressure, and water was added to the residue. The mixture was adjusted to pH 12-13 by addition of 2 N NaOH, and extracted with ethyl acetate (150 ml, 100 ml). The extract was dried over anhydrous sodium sulfate. The ethyl acetate was evaporated under reduced pressure, and the resultant residue was recrystallized from ethyl acetate-petroleum ether to give 5-amino-4-(2-chloro-6-fluorobenzyl)amino-6-methylaminopyrimidine as brown crystals (671 mg, yield 79%), m.p. 210°-213° C.

Workup

  1. additionwas added portionwise to the solution
  2. stirringThe mixture was stirred at the same temperature for 30 minutes
  3. concentrationafter which it was concentrated to dryness under reduced pressure, and water
  4. additionwas added to the residue
  5. additionThe mixture was adjusted to pH 12-13 by addition of 2 N NaOH
  6. extractionextracted with ethyl acetate (150 ml, 100 ml)
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customThe ethyl acetate was evaporated under reduced pressure
  9. customthe resultant residue was recrystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-0bcb71faf34a45d2bde4340aa99b313c
Source dataset
uspto-grants-1983_12
Patent number
US04423219

Reaction notes

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