Benzyl Bromide → 5-benzyl-2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

HRID 1631727Notes

Reaction equation

HRID 1631727 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1.[Li].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([N:8]1[C:7](=[O:12])[CH:6]2[CH2:13][O:14][CH2:15][CH2:16][N:5]2[C:4]2[N:3]=[C:2]([Cl:1])[N:11]=[CH:10][C:9]1=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 3028194LithiumHCID 866515602-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Product 1

HCID 866701145-benzyl-2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in a manner similar to PREPARATION x38 using 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x1, 500 mg, 2.078 mmol), 1M lithium bis(trimethylsiylyamide) in hexanes (2.493 mL, 2.493 mmol) and (bromomethyl)benzene (0.271 mL, 2.286 mmol) in DMF (10 mL) at 0° C. for 18 hours. 1H NMR (400 MHz, DMSO-d6) δ 2.94-3.06 (m, 1H), 3.50-3.61 (m, 1H), 3.62-3.72 (m, 1H), 3.90-3.99 (m, 1H), 4.17-4.32 (m, 2H), 4.56-4.67 (m, 1H), 5.02-5.22 (m, 2H), 7.29 (s, 5H), 7.72 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C16H15ClN4O2, 331.09. found 331.2.

Sources & evidence

ORD record
ord-3f3b8a6e83bb45a9a3f443674c580ae8
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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