Tert-Butylamine → HCID 19073890, compound

HRID 2367285Notes

Reaction equation

HRID 2367285 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[CH3:10][C:11]([NH2:14])([CH3:13])[CH3:12].C(N(CC)CC)C>CC#N>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH:14][C:11]([CH3:13])([CH3:12])[CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 19073890HCID 19073890, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
170 °C

Procedure

To 4,6-dichloro-2-pyrimidinamine (400 mg, 2.44 mmol) in CH3CN (5 mL) were added (1,1-dimethylethyl)amine (0.34 mL, 3.17 mmol) and triethylamine (1.36 mL, 9.76 mmol), and the reaction mixture was heated in a microwave at 170° C. for a total of 2.25 hours, checking the progression of the reaction at regular intervals. The mixture was cooled down and evaporated. The resulting residue was partitioned between EtOAc and water, and extracted with EtOAc (2×) and CH2Cl2 (2×). The organics were washed with water and brine, dried (MgSO4), filtered and evaporated. The resulting solid was triturated with Et2O and dried in vacuo to afford the title compound (440 mg). LC-MS (ES) m/z=201, 203 [M+H]+.

Workup

  1. customthe progression of the reaction at regular intervals
  2. temperatureThe mixture was cooled down
  3. customevaporated
  4. customThe resulting residue was partitioned between EtOAc and water
  5. extractionextracted with EtOAc (2×) and CH2Cl2 (2×)
  6. washThe organics were washed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe resulting solid was triturated with Et2O
  11. customdried in vacuo

Sources & evidence

ORD record
ord-d8f87ae2f8dd45ca8ebc71b97d53936f
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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