tert-Butyl piperazine-1-carboxylate → HCID 67460900, compound

HRID 625044Notes

Reaction equation

HRID 625044 reaction equation
Cl[C:2]1[C:3]2[CH:10]([CH2:11][CH3:12])[S:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>CCCCO>[CH2:11]([CH:10]1[C:3]2[C:2]([N:23]3[CH2:22][CH2:21][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:25][CH2:24]3)=[N:7][CH:6]=[N:5][C:4]=2[CH2:8][S:9]1)[CH3:12]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 86675326HCID 86675326, compound

Product 1

HCID 67460900HCID 67460900, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 4-chloro-5-ethyl-5,7-dihydrothieno[3,4-d]pyrimidine (0.3 g, 1.5 mmol) in n-BuOH (30 mL) was added 1-Boc-piperazine (0.8 g, 4.3 mmol), and the mixture was refluxed for 30 hours. The solvent was removed and the residue was purified by silica gel chromatography, eluting with Hexane/ethyl acetate (4:1-1:1) to give tert-butyl 4-(5-ethyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylate (0.23 g, 44%). 1H NMR (CDCl3, 400 MHz) δ 8.54 (s, 1H), 4.61 (d, J=8.8 Hz, 1H), 4.10 (m, 2H), 3.80-3.60 (m, 8H), 2.02 (m, 1H), 1.60 (m, 1H), 1.49 (s, 9H), 0.95 (m, 3H). MS (APCI+) [M+H]+ 351.

Workup

  1. temperaturethe mixture was refluxed for 30 hours
  2. customThe solvent was removed
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with Hexane/ethyl acetate (4:1-1:1)

Sources & evidence

ORD record
ord-5ebc32c02e8745068681b005c2a06bae
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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