4-Amino-1-Boc-piperidine → HCID 86671079, compound

HRID 1485537Notes

Reaction equation

HRID 1485537 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][N:8]=[C:9](OC3CCOCC3)[C:10]=2[N:11]=1.[NH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1.CC(C)([O-])C.[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:19][CH:20]3[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]3)[C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 12682914-Amino-1-Boc-piperidineHCID 23676156Sodium t-butoxideHCID 866710656-chloro-4-[(tetrahydro-2H-pyran-4-yl)oxy]-Pyrido[3,2-d]pyrimidine2×

Product 1

HCID 86671079HCID 86671079, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4,6-dichloropyrido[3,2-d]pyrimidine (Intermediate 1, step D) (0.100 g, 0.500 mmol), tert-butyl 4-aminopiperidine-1-carboxylate (0.110 g, 0.550 mmol), PdCl2(dppf)-CH2Cl2Adduct (4.08 mg, 5.00 μmol) and sodium tert-butoxide (0.096 g, 1.00 mmol) in dioxane (2.50 ml) was refluxed for 4 hours After cooling to room temperature, the reaction mixture was filtered through a Celite pad and washed with CH2Cl2. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=1:1) to give tert-butyl 4-(6-chloropyrido[3,2-d]pyrimidin-4-ylamino)piperidine-1-carboxylate (0.089 g, 49%) as a yellow solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 1.49 (9H, s), 1.52-1.75 (2H, m), 2.05-2.16 (2H, m), 2.92-3.10 (2H, m), 4.08-4.25 (2H, m), 4.35-4.42 (1H, m), 6.87 (1H, d, J=8.4 Hz), 7.63 (1H, d, J=8.8 Hz), 8.06 (1H, d, J=8.8 Hz), 8.62 (1H, s).

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationthe reaction mixture was filtered through a Celite pad
  3. washwashed with CH2Cl2
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography on SiO2 (Hex:EtOAc=1:1)

Sources & evidence

ORD record
ord-630844cfa8dd40a7bacf0e43b8c6478a
Source dataset
uspto-grants-2016_08
Patent number
US09422298B2

Reaction notes

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