Triethylamine → Tert-butyl 2-(2-amino-5-bromo-6-chloropyrimidin-4-ylamino)ethylcarbamate

HRID 2401443

Reaction equation

HRID 2401443 reaction equation
[Br:1][C:2]1[C:3]([Cl:10])=[N:4][C:5]([NH2:9])=[N:6][C:7]=1Cl.C(N(CC)CC)C.[NH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25]>CN(C=O)C>[NH2:9][C:5]1[N:6]=[C:7]([NH:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[C:2]([Br:1])=[C:3]([Cl:10])[N:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 6182885-Bromo-4,6-dichloropyrimidin-2-amine

Product 1

HCID 86649359Tert-butyl 2-(2-amino-5-bromo-6-chloropyrimidin-4-ylamino)ethylcarbamateYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 5-bromo-4,6-dichloropyrimidin-2-amine (Reference Example 1, 14.00 g, 0.0576 mole), and triethylamine (41.8 mL, 0.2997 mole) in DMF (55 mL) was treated with tert-butyl 2-aminoethylcarbamate (9.24 g, 0.0576 mole). The reaction mixture was stirred at ambient temperature for 18 hours, then volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give a yellow solid that was triturated with ether to remove color. The ether-insoluble material was collected by filtration and dried under vacuum to provide tert-butyl 2-(2-amino-5-bromo-6-chloropyrimidin-4-ylamino)ethylcarbamate (18.02 g, 85.2% yield). 1H NMR (300 MHz, CD3OD) δ ppm 1.42 (s, 9H), 3.25 (t, J=6 Hz, 2H), 3.47 (t, J=6 Hz, 2H). MS (DCl—NH3) m/z=366 (M+H)+.

Workup

  1. customvolatiles were removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give a yellow solid
  7. customthat was triturated with ether
  8. customto remove color
  9. filtrationThe ether-insoluble material was collected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-d33d021893794aca8761e40da279e3e3
Source dataset
uspto-grants-2014_08
Patent number
US08796297B2

Linked notes

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