2-Amino-4,6-dichloropyrimidine → HCID 31537986, compound

HRID 2401448Notes

Reaction equation

HRID 2401448 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(N(C(C)C)C(C)C)C>C(O)C>[NH2:9][C:4]1[N:3]=[C:2]([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)[CH:7]=[C:6]([Cl:8])[N:5]=1

Participants

5

Reactant 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 31537986HCID 31537986, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4,6-dichloropyrimidin-2-amine (1.500 g, 0.0091 mole), tert-butyl piperazine-1-carboxylate (2.044 g, 0.0110 mole), and N-ethyl-N-isopropylpropan-2-amine (11.1 mL, 0.0637 mole) in ethanol (20 mL) was magnetically stirred in a sealed tube at 80° C. for 18 hours. After cooling to ambient temperature, the seal was broken and volatiles were removed under reduced pressure. 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 crude, white solid that was crystallized from hot methanol. The crystals were collected by filtration and dried under vacuum to provide tert-butyl 4-(2-amino-6-chloropyrimidin-4-yl)piperazine-1-carboxylate (1.95 g, 68.3% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.48 (s, 9H), 3.46-3.52 (m, 4H), 3.55-3.61 (m, 4H), 4.90 (sbr, 2H), 5.96 (s, 1H). MS (DCl—NH3) m/z=314 (M+H)+.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customvolatiles were removed under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto give a crude, white solid
  8. customthat was crystallized from hot methanol
  9. filtrationThe crystals were collected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-a2bfe32f9ffc4743b3808b46acbb7a95
Source dataset
uspto-grants-2014_08
Patent number
US08796297B2

Reaction notes

Loading…