N,N-Dimethylaniline → HCID 10933636, compound

HRID 840341Notes

Reaction equation

HRID 840341 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[N:7]=1.CN(C)C1C=CC=CC=1.[CH:25]([OH:28])([CH3:27])[CH3:26]>C(OCC)(=O)C>[CH3:13][O:12][C:10]1[CH:9]=[C:8]([O:14][CH3:15])[N:7]=[C:6]([NH:5][C:1](=[O:2])[O:28][CH:25]([CH3:27])[CH3:26])[N:11]=1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 3776IsopropanolHCID 6371Phosgene2×HCID 1189462-Amino-4,6-dimethoxypyrimidine

Product 1

HCID 10933636HCID 10933636, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Conditions

Temperature
22.5 °C

Procedure

Phosgene (20 g, 202 mmol) was passed at 20-25° C. in the course of 45 min into a recipient vessel of ethyl acetate (120 ml). A solution of 2-amino4,6-dimethoxypyrimidine (15.6 g, 101 mmol) and N,N-dimethyl-aniline (26 ml, 203 mmol) in ethyl acetate (90 ml) was added dropwise at 25° C. in the course of 3 h. After 15 min, the suspension was aerated with nitrogen until it was free of phosgene, ethyl acetate (120 ml) was added and isopropanol (10 ml, 130 mmol) was added dropwise in the course of 10 min with cooling (20-25° C.). The reaction was filtered after 1 h, washed with ethyl acetate (3×20 ml) and the combined filtrates were extracted with hydrochloric acid (1.0 N, 2×30 ml) and water (2×30 ml). The solution was then concentrated and the product was crystallized from the residue; yield 19.2 g (80% of theory), m.p. 51-54° C.

Workup

  1. additionwas added
  2. filtrationThe reaction was filtered after 1 h
  3. washwashed with ethyl acetate (3×20 ml)
  4. extractionthe combined filtrates were extracted with hydrochloric acid (1.0 N, 2×30 ml) and water (2×30 ml)
  5. concentrationThe solution was then concentrated
  6. customthe product was crystallized from the residue

Sources & evidence

ORD record
ord-5ee1ee606ce14e7aac9d2a669ec0d2d5
Source dataset
uspto-grants-2002_04
Patent number
US06365739B1

Reaction notes

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