Triethylamine → HCID 11255508, compound

HRID 1192420Notes

Reaction equation

HRID 1192420 reaction equation
Cl[C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[N:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(N(CC)CC)C>ClCCCl.CC(O)C>[C:15]([O:14][C:12]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[C:3]3[CH:11]=[CH:10][CH:9]=[N:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:21][CH2:20]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5690394-Chloropyrido[2,3-d]pyrimidine

Product 1

HCID 11255508HCID 11255508, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 4-chloropyrido[2,3-d]pyrimidine (0.72 g, 4.4 mmol) and 1-Boc piperazine (0.84 g, 4.5 mmol) in DCE (10 mL) and IPA (10 mL) was added triethylamine (4 mL). The mixture was refluxed for 4 hours. After cooling, the solvent was removed. The residue was subject to column chromatography by ethyl acetate to give 4-pyrido[2,3-d]pyrimidin-4-yl-piperazine-1-carboxylic acid tert-butyl ester (1.26 g, 92%). 1H NMR (CDCl3, 400 MHz) δ 9.07 (dd, J=4.30 Hz, J=1.98 Hz, 1H), 8.88 (s, 1H), 8.25 (dd, J=7.99 Hz, J=1.98 Hz, 1H), 7.41 (dd, J=8.18 Hz, J=3.74 Hz, 1H), 3.82 (m, 4H), 3.65 (m, 4H), 1.50 (s, 9H). MS (APCI+) [M+H]+316.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperatureAfter cooling
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-daa4800933464bc3af794efde3cc5a99
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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