2-Bromo-6-(bromomethyl)pyridine → 5-((6-Bromopyridin-2-yl)methyl)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

HRID 2169556Notes

Reaction equation

HRID 2169556 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][CH2:7][CH:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1.CC(C)([O-])C.[Na+].[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Br)[N:24]=1>CS(C)=O>[Br:22][C:23]1[N:24]=[C:25]([CH2:29][N:8]2[CH2:7][CH:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]3[N:3]=[C:2]([Cl:1])[N:11]=[CH:10][C:9]2=3)[CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 23676156Sodium t-butoxideHCID 86670087HCID 86670087, compound

Product 1

HCID 866701045-((6-Bromopyridin-2-yl)methyl)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in a manner similar to PREPARATION x9 using 2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 300 mg, 1.324 mmol) in DMSO (20 mL) followed by sodium tert-butoxide (153 mg, 1.588 mmol) and 2-bromo-6-(bromomethyl)pyridine (332 mg, 1.324 mmol). 1H NMR (400 MHz, DMSO-d6) δ 2.92-3.04 (m, 1 H), 3.12-3.24 (m, 2 H), 3.40-3.53 (m, 2 H), 3.62-3.72 (m, 1 H), 3.86-4.00 (m, 2 H), 4.19-4.28 (m, 1 H), 4.42-4.64 (m, 2 H), 7.31 (s, 4 H), 7.36-7.43 (m, 4 H), 7.56 (s, 3 H), 7.72 (d, J=7.83 Hz, 4 H). ESI-MS m/z [M+H]+ calc'd for C15H15BrClN5O, 396.01; found 396.1.

Sources & evidence

ORD record
ord-86f8e1dec6b24e64825e4da489d0c4d2
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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