2,4-Dichloroquinazoline → HCID 86600305, compound

HRID 729531Notes

Reaction equation

HRID 729531 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.[C:13]([O:17][C:18]([N:20]1[CH2:25][C@@H:24]2[CH2:26][C@H:21]1[CH2:22][NH:23]2)=[O:19])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:18]([N:20]1[CH2:25][C@@H:24]2[CH2:26][C@H:21]1[CH2:22][N:23]2[C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([Cl:1])[N:11]=1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

3

Reactant 2

HCID 2528862,4-DichloroquinazolineHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 86600305HCID 86600305, compound

Conditions

Temperature
60 °C

Procedure

To a solution of 2,4-dichloro-quinazoline (0.25 g, 1.26 mmol) in isoprapanol (6 mL) were added t-butyl-(1S,4S)-(−)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.25 g, 1.26 mmol) and the solution was heated at 60° C. for 4 h. The reaction was concentrated in vacuo and the residue was chromatographed over silica with 25:10:65, 35:10:55, and 50:10:40 EtOAc-CH2Cl2-Hexane; 1%, 3%, and 5% MeOH/CH2Cl2 to give the title compound. MS (ES+): 361.1 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was chromatographed over silica with 25:10:65, 35:10:55, and 50:10:40 EtOAc-CH2Cl2-Hexane

Sources & evidence

ORD record
ord-e3721981856f457b89ebae0a5b34c7eb
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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