tert-Butyl piperazine-1-carboxylate → HCID 67457495, compound

HRID 625049Notes

Reaction equation

HRID 625049 reaction equation
Cl[C:2]1[C:3]2[CH2:10][S:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>C(O)(C)C>[N:5]1[C:4]2[CH2:8][S:9][CH2:10][C:3]=2[C:2]([N:21]2[CH2:20][CH2:19][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:23][CH2:22]2)=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 457897284-Chloro-5,7-dihydrothieno[3,4-d]pyrimidine

Product 1

HCID 67457495HCID 67457495, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The mixture of 4-chloro-5,7-dihydrothieno[3,4-d]pyrimidine (2.0 g, 11.6 mmol) and 1-Boc-piperazine (5.0 g, 26.8 mmol) in isopropanol (50 mL) was refluxed for 12 hours. The solvent was removed and the residue was subject to silica gel chromatography, eluting with hexane/ethyl acetate (1:1) to give tert-butyl 4-(5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylate (3.3 g, 89%). 1H NMR (CDCl3, 400 MHz) δ 8.49 (s, 1H), 4.68 (m, 1H), 4.25 (s, 2H), 4.16 (s, 2H), 1.49 (s, 9H). MS (APCI+) [M+H]+ 323.

Workup

  1. temperaturewas refluxed for 12 hours
  2. customThe solvent was removed
  3. washeluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-a13be88e5d9f44a592ff4a2a4aa93eaa
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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