Triethylamine → Tert-butyl 2-(2-aminopyrimidin-4-ylamino)ethylcarbamate

HRID 2386977Notes

Reaction equation

HRID 2386977 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[NH2:12][C:13]1[N:18]=[CH:17][CH:16]=[C:15](Cl)[N:14]=1.C(N(CC)CC)C>COCCO.C(Cl)Cl>[NH2:12][C:13]1[N:18]=[C:17]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])[CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 2233322-Amino-4-chloropyrimidine

Product 1

HCID 68602141Tert-butyl 2-(2-aminopyrimidin-4-ylamino)ethylcarbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
130 °C

Procedure

tert-Butyl 2-aminoethylcarbamate (3.27 g, 20.4 mmol) and 2-amino-6-chloropyrimidine (2.38 g, 18.4 mmol) were combined in 2-methoxyethanol with triethylamine (4.3 mL, 30.3 mmol) and heated to 130° C. overnight. The mixture was diluted with methylene chloride and washed with 1 N sodium hydroxide. The aqueous layer was extracted with methylene chloride followed by ethyl acetate. The organic layers were combined, absorbed on silica gel, and purified using silica gel chromatography, eluting with a gradient of methanol in methylene chloride (1-12%) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.44 (s, 9H) 3.32 (q, J=5.31 Hz, 2H) 3.38-3.50 (m, 2H) 4.70 (s, 2H) 4.91-5.19 (m, 2H) 5.78 (d, J=5.76 Hz, 1H) 7.81 (d, J=5.76 Hz, 1H); MS (ESI+) m/z 253.9 (M+H)+.

Workup

  1. washwashed with 1 N sodium hydroxide
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. customabsorbed on silica gel
  4. custompurified
  5. washeluting with a gradient of methanol in methylene chloride (1-12%)

Sources & evidence

ORD record
ord-66e94c66c2444b7c814ebcc81af33096
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

Loading…