Water → HCID 13649693, compound

HRID 1248888Notes

Reaction equation

HRID 1248888 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4](Cl)[N:3]=1.[CH3:11][O:12][CH2:13][CH2:14][CH2:15][NH2:16].O>O1CCCC1>[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([NH:16][CH2:15][CH2:14][CH2:13][O:12][CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 16723-MethoxypropylamineHCID 158501962,5,6-Trichloropyrimidin-4-amine

Product 1

HCID 13649693HCID 13649693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,850 g (9.31 moles) of 4-amino-2,5,6-trichloropyrimidine are dissolved in 4 liters of tetrahydrofuran. 1,659 g (18.62 moles) of 3-methoxypropylamine are added dropwise thereto over a period of 6 hours. The reaction mixture is heated for five hours at the boil, cooled and stirred into 20 liters of water. The resulting solid is filtered off, dried, stirred with 7 liters of methylene chloride and again filtered off. After the solid thus obtained has been twice recrystallised from toluene, 743 g (31.8% of theory) of the desired pyrimidine, melting point 114° C., are obtained.

Workup

  1. temperatureThe reaction mixture is heated for five hours at the boil
  2. temperaturecooled
  3. filtrationThe resulting solid is filtered off
  4. customdried
  5. filtrationagain filtered off
  6. customAfter the solid thus obtained
  7. customhas been twice recrystallised from toluene, 743 g (31.8% of theory) of the desired pyrimidine, melting point 114° C.
  8. customare obtained

Sources & evidence

ORD record
ord-9d533af01f50450198be8d99d62358dd
Source dataset
uspto-grants-1986_12
Patent number
US04627872

Reaction notes

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