Neopentylamine → HCID 19428494, compound

HRID 1078944Notes

Reaction equation

HRID 1078944 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([NH:9][C:10]([CH3:13])([CH3:12])[CH3:11])[N:3]=1.[NH2:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17]>C(O)(C)C>[Cl:8][C:6]1[N:7]=[C:2]([NH:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:3]=[C:4]([NH:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=1

Participants

4

Reactant 2

HCID 79882NeopentylamineHCID 19428522HCID 19428522, compound

Product 1

HCID 19428494HCID 19428494, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

After dissolving 5.0 g of 2,4-dichloro-6-(1,1-dimethylethylamino)pyrimidine in 25 ml of isopropanol and adding 5 ml of 1-amino-2,2-dimethylpropane, the reaction mixture is boiled under reflux for 20 hours. Subsequently, the reaction mixture is evaporated and the residue is distributed between 80 ml of chloroform and 15 ml of 10% sodium hydroxide solution. After separation the organic phase is washed 4 times with 20 ml of water each, then dried and evaporated. The evaporation residue is purified by chromatography on a silica gel column by using a 9:1 mixture of hexane/ethyl acetate as eluent. After recrystallizing the eluted product from hexane, the title product is obtained in a yield of 4.05 g (65.9%), m.p.: 115°-119° C.

Workup

  1. temperatureunder reflux for 20 hours
  2. customSubsequently, the reaction mixture is evaporated
  3. customAfter separation the organic phase
  4. washis washed 4 times with 20 ml of water each,
  5. customthen dried
  6. customevaporated
  7. customThe evaporation residue is purified by chromatography on a silica gel column
  8. additiona 9:1 mixture of hexane/ethyl acetate as eluent
  9. customAfter recrystallizing the eluted product from hexane

Sources & evidence

ORD record
ord-a987430f24e745ad889ce02b1a2948f6
Source dataset
uspto-grants-1996_08
Patent number
US05550240

Reaction notes

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