2-Amino-5-bromopyridine → 6-(6-Amino-pyridin-3-yl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

HRID 1635005Notes

Reaction equation

HRID 1635005 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH3:9][C:10]1([CH3:24])[C:15]2[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][C:14]=2[NH:13][C:12](=[O:23])[O:11]1>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:17]2[CH:18]=[CH:19][C:14]3[NH:13][C:12](=[O:23])[O:11][C:10]([CH3:24])([CH3:9])[C:15]=3[CH:16]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 10987806(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acid

Product 1

HCID 120945046-(6-Amino-pyridin-3-yl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Procedure

Prepared according to procedure B from 2-amino-5-bromopyridine and (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid. White crystals, mp 257-259° C. 1H-NMR (DMSO-d6) δ10.20 (s, 1H), 8.22 (d,1H, J=2.38 Hz) 7.69,7.66 (dd, 1H, J=2.5, 2.5 Hz), 7.42 (m,2H), 6.89 (d,1H, J=8.8 Hz), 6.49 (d, 1H, J=8.64 Hz), 6.02 (s,2H), 1.64 (s,6H); MS m/z 269 M+. Anal. Calcd. For C15H15N3O2.17H2O: C, 66.15, H, 5.68, N, 15.43. Found C, 66.10, H, 5.81, N, 15.02.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-829fcf1a3a29483bb7493f59d1a953d7
Source dataset
uspto-grants-2003_01
Patent number
US06509334B1

Reaction notes

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