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

HRID 2401444Notes

Reaction equation

HRID 2401444 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:5](Br)=[C:4](Cl)[N:3]=1.C(N(CC)CC)C.[H][H]>[Pd].C(OCC)(=O)C.CO>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86649359Tert-butyl 2-(2-amino-5-bromo-6-chloropyrimidin-4-ylamino)ethylcarbamateHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of tert-butyl 2-(2-amino-5-bromo-6-chloropyrimidin-4-ylamino)ethylcarbamate (Example 1A, 18.60 g, 0.0507 mole), triethylamine (135.0 mL, 0.9686 mole), and 10% palladium on charcoal (7.40 g) in 1:1 ethyl acetate/methanol (500 mL) was treated with hydrogen (60 psi) for two days. Insoluble material was removed by filtration through a pad of diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and dilute aqueous sodium hydroxide. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give tert-butyl 2-(2-aminopyrimidin-4-ylamino)ethylcarbamate as a white, amorphous solid (12.7 g, 98.8% yield). 1H NMR (300 MHz, CD3Cl3) δ ppm 1.44 (s, 9H), 3.27-3.37 (m, 2H), 3.37-3.47 (m, 2H), 5.00 (sbr, 2H), 5.28 (sbr, 1H), 5.52 (sbr, 1H), 5.78 (d, J=6 Hz, 1H), 7.76 (d, J=6 Hz, 1H). MS (DCl—NH3) m/z=254 (M+H)+.

Workup

  1. customInsoluble material was removed by filtration through a pad of diatomaceous earth
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and dilute aqueous sodium hydroxide
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-67d771c486544bfb8e850714a9ea605b
Source dataset
uspto-grants-2014_08
Patent number
US08796297B2

Reaction notes

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