2,4-Dichloroquinazoline → tert-Butyl 4-((2-chloroquinazolin-4-yl)amino)piperidine-1-carboxylate

HRID 215919Notes

Reaction equation

HRID 215919 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1>C1COCC1.CN(C1C=CN=CC=1)C.CCOC(C)=O.CCCCCC>[Cl:1][C:2]1[N:11]=[C:10]([NH:13][CH:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 2

HCID 2528862,4-DichloroquinazolineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 58006142tert-Butyl 4-((2-chloroquinazolin-4-yl)amino)piperidine-1-carboxylate

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-dichloroquinazoline (2 g, 10.05 mmol) in THF (50 ml) at 0° C. was added tert-butyl 4-aminopiperidine-1-carboxylate (2.2 g, 11.05 mmol), followed by TEA (2.8 ml, 20.1 mmol) and catalyst DMAP (3 mg). The reaction mixtures was then warmed up to room temperature and stirred for 20 hours. The product was extracted with EtOAc (×2). The organic layers were combined and washed with water, and brine, and dried (MgSO4) and concentrated under vacuum. The product was isolated after silica gel column chromatography using 20% EtOAc and 80% hexane as eluent.

Workup

  1. customThe reaction mixtures
  2. extractionThe product was extracted with EtOAc (×2)
  3. washwashed with water, and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under vacuum
  6. customThe product was isolated after silica gel column chromatography

Sources & evidence

ORD record
ord-892a4d3ccbb04aba8683abc10bdee82a
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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