N-((3S,4S)-4-azidotetrahydro-2H-pyran-3-yl)-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-amine → (3S,4S)-N3-(6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)tetrahydro-2H-pyran-3,4-diamine

HRID 56380Notes

Reaction equation

HRID 56380 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][O:7][CH2:6][C@H:5]1[NH:10][C:11]1[N:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:21]3[C:26]([Cl:27])=[C:25]([O:28][CH3:29])[CH:24]=[C:23]([O:30][CH3:31])[C:22]=3[Cl:32])[CH:17]=2)[N:12]=1)=[N+]=[N-]>CO.CCOC(C)=O.[Pd]>[Cl:27][C:26]1[C:25]([O:28][CH3:29])=[CH:24][C:23]([O:30][CH3:31])=[C:22]([Cl:32])[C:21]=1[C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([NH:10][C@H:5]1[C@@H:4]([NH2:1])[CH2:9][CH2:8][O:7][CH2:6]1)[N:20]=[CH:19]2

Participants

5

Reactant 1

HCID 118036528N-((3S,4S)-4-azidotetrahydro-2H-pyran-3-yl)-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-amine

Product 1

HCID 118036332(3S,4S)-N3-(6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)tetrahydro-2H-pyran-3,4-diamineYield 101%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-((3S,4S)-4-azidotetrahydro-2H-pyran-3-yl)-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-amine (0.063 g, 0.133 mmol) was taken up in Methanol (7 ml) and EtOAc (7.00 ml), Pd—C (0.014 g, 0.133 mmol) was added and stirred under a H2 balloon for 1 hour. After the reaction was completed, it was filtered through celite and the solvent removed. (3S,4S)—N3-(6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)tetrahydro-2H-pyran-3,4-diamine (0.060 g, 0.134 mmol, 101% yield) was recovered as a yellow solid, which was carried on without further purification. MS (ES+) C21H22Cl2N4O3 requires: 448, found: 449 [M+H]+.

Workup

  1. filtrationit was filtered through celite
  2. customthe solvent removed

Sources & evidence

ORD record
ord-2cf81d1680474f83bd91582dbadfcbb6
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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