Triethylamine → 6-Chloro-N2-ethylpyrimidine-2,4-diamine

HRID 860078Notes

Reaction equation

HRID 860078 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.Cl.[CH2:11]([NH2:13])[CH3:12].CCN(CC)CC>C(O)CCC>[NH2:8][C:6]1[CH:5]=[C:4]([Cl:9])[N:3]=[C:2]([NH:13][CH2:11][CH3:12])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 823874-Pyrimidinamine, 2,6-dichloro-

Product 1

HCID 234355296-Chloro-N2-ethylpyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,6-dichloro-4-aminopyrimidine 18-1 (Avocado; 4.8 g, 29.3 mmol), ethylamine hydrochloride (7.0 g, 85.8 mmol), Et3N (20 mL, 144 mmol) and n-butanol (150 mL) was heated to 90° C. for 6 hours. After cooling, the solvent was removed in vacuo and the residue partitioned between saturated Na2CO3 solution and EtOAc. The EtOAc layer was washed with brine, dried (MgSO4) and concentrated to give an orange solid. Purification by column chromatography (EtOAc/hexane 1:1) gave the title compound 18-2 as a white solid.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. customthe residue partitioned between saturated Na2CO3 solution and EtOAc
  4. washThe EtOAc layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give an orange solid
  8. customPurification by column chromatography (EtOAc/hexane 1:1)

Sources & evidence

ORD record
ord-f375066a496849a29a18fbc735d95bb3
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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