HCID 19428522, compound → HCID 19428515, compound

HRID 1078939Notes

Reaction equation

HRID 1078939 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:5]=[C:4]([Cl:13])[N:3]=1>NC(C)(C)C>[Cl:13][C:4]1[N:3]=[C:2]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])[N:7]=[C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:5]=1

Participants

3

Reactant 1

HCID 19428522HCID 19428522, compound

Product 1

HCID 19428515HCID 19428515, compound

Reagents, catalysts & solvents 1

HCID 6385Tert-ButylamineSolvent

Procedure

A solution of 10 g of 2,6-dichloro-4-(1,1-dimethylethylamino)pyrimidine in 50 ml of 1-amino-1,1-dimethylethane is heated in a closed tube at 130° C. for 15 hours. Thereafter, the reaction mixture is evaporated and the residue is distributed between 150 ml of chloroform and 30 ml of 10% sodium hydroxide solution. After separation the organic phase is washed 4 times with 10 ml of water each, then dried and evaporated. The evaporation residue is subjected to chromatography on a silica gel column by using a 9:1 mixture of hexane/ethyl acetate as eluent to give 6-chloro-2,4-bis(1,1-dimethylethylamino) pyrimidine which is recrystallized from hexane to result in a yield of 9.92 g (85.1%), m.p.: 125°-127° C. By continuing the elution with a 4:1 mixture of hexane/ethyl acetate 2-chloro-4,6-bis(1,1-dimethylethylamino)pyrimidine as a more polar product is obtained which is recrystallized from hexane to result in a yield of 0.49 g (4.2%), m.p.: 132°-135° C.

Workup

  1. customThereafter, the reaction mixture is evaporated
  2. customAfter separation the organic phase
  3. washis washed 4 times with 10 ml of water each,
  4. customthen dried
  5. customevaporated
  6. additiona 9:1 mixture of hexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-f357e850832d48708f1770e1315aa484
Source dataset
uspto-grants-1996_08
Patent number
US05550240

Reaction notes

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