1-Acetoxy-2-bromoethane → (R)-2-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)ethanol

HRID 1631743Notes

Reaction equation

HRID 1631743 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][CH2:7][C@@H:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1.[CH3:16][C:17](C)([O-:19])C.[Na+].C(OCCBr)(=O)C>CS(C)=O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:16][CH2:17][OH:19])[CH2:7][C@@H:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 135641-Acetoxy-2-bromoethaneHCID 23676156Sodium t-butoxideHCID 86670088(R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Product 1

HCID 86670127(R)-2-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)ethanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in a manner similar to PREPARATION x5 using (R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 100 mg, 0.441 mmol) in DMSO (7 mL), sodium tert-butoxide (51 mg, 0.529 mmol) and bromoethyl acetate (81 mg, 0.485 mmol) (79 mg, 66%). ESI-MS m/z [M+H]+ calc'd for C11H15ClN4O2, 271.09. found 271.1.

Sources & evidence

ORD record
ord-6e4ffc12e0e64785bb8ba8deeb61ba44
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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