Boron tribromide → N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-hydroxyphenyl]benzenesulphonamide

HRID 611548Notes

Reaction equation

HRID 611548 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])=[C:13]([O:27]C)[CH:12]=3)=[CH:9][N:8]([CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[C:4]=2[N:5]=[CH:6][N:7]=1.B(Br)(Br)Br>ClCCl>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])=[C:13]([OH:27])[CH:12]=3)=[CH:9][N:8]([CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9956039N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzenesulphonamide

Product 1

HCID 15429252N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-hydroxyphenyl]benzenesulphonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Example 33, N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzenesulphonamide was reacted with boron tribromide in dichloromethane at -10° C. to give N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-hydroxyphenyl]benzenesulphonamide, m.p. 265-267° C. The structure was confirmed by 1H nmr and mass spectra.

Sources & evidence

ORD record
ord-ddbd2ed88a9c4c8cb8c0f028b6f37268
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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