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

HRID 2169583Notes

Reaction equation

HRID 2169583 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.CC(C)([O-])C.[Na+].Br[CH2:23][CH2:24][C:25]([CH3:28])([OH:27])[CH3:26]>CS(C)=O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:23][CH2:24][C:25]([CH3:28])([OH:27])[CH3:26])[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 106071724-Bromo-2-methylbutan-2-olHCID 23676156Sodium t-butoxideHCID 86670088(R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Product 1

HCID 86670126(R)-4-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)-2-methylbutan-2-ol

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, 300 mg, 1.324 mmol) in DMSO (7 mL), sodium tert-butoxide (153 mg, 1.588 mmol) and 4-bromo-2-methylbutan-2-ol (243 mg, 1.456 mmol) (306 mg, 74%). ESI-MS m/z [M+H]+ calc'd for C14H21ClN4O2, 313.14; found 313.2.

Sources & evidence

ORD record
ord-86992bfa3a7e4cb88b489eca1add7253
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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