Triethylamine → HCID 86691180, compound

HRID 333093Notes

Reaction equation

HRID 333093 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH2:10])[CH:3]=1.[NH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[NH2:10][C:4]1[N:5]=[C:6]([S:8][CH3:9])[N:7]=[C:2]([NH:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 704964-Amino-6-chloro-2-methylthiopyrimidineHCID 187201N-BOC-ethylenediamine

Product 1

HCID 86691180HCID 86691180, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

6-Chloro-2-methylsulfanyl-pyrimidin-4-amine (176 mg, 1 mmol) was dissolved together with tert-butyl N-(2-aminoethyl)carbamate (200 mg, 1.25 mmol) and triethylamine (174 μl, 1.25 mmol) in THF (2 ml). The mixture was stirred at 180° C. under microwave heating for 8 hours. The mixture was diluted with ethyl acetate and the resulting solution was washed with a solution of sodium bicarbonate (5%) and brine, dried over magnesium sulfate, the volatiles were removed under reduced pressure. The residue dissolved in DCM and purified by filtration over silica to yield 105 mg (0.35 mmol, 35%) MS (ESI) m/z=300.2 [M+1]+.

Workup

  1. temperatureheating for 8 hours
  2. washthe resulting solution was washed with a solution of sodium bicarbonate (5%) and brine
  3. dry with materialdried over magnesium sulfate
  4. customthe volatiles were removed under reduced pressure
  5. dissolutionThe residue dissolved in DCM
  6. filtrationpurified by filtration over silica
  7. customto yield 105 mg (0.35 mmol, 35%)

Sources & evidence

ORD record
ord-1221f2fba64048baab87a1f078591465
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

Loading…