5-(Chloromethyl)-1,3-oxazole → (R)-2-chloro-5-(oxazol-5-ylmethyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

HRID 1631745Notes

Reaction equation

HRID 1631745 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+].Cl[CH2:23][C:24]1[O:28][CH:27]=[N:26][CH:25]=1>CS(C)=O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:23][C:24]3[O:28][CH:27]=[N:26][CH:25]=3)[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 152908805-(Chloromethyl)-1,3-oxazoleHCID 23676156Sodium t-butoxideHCID 86670088(R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Product 1

HCID 86670129(R)-2-chloro-5-(oxazol-5-ylmethyl)-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 x5 using (R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 351 mg, 1.547 mmol) in DMSO (10 mL), sodium tert-butoxide (178 mg, 1.856 mmol) and 5-(chloromethyl)oxazole (200 mg, 1.702 mmol) (171 mg, 36%). ESI-MS m/z [M+H]+ calc'd for C13H14ClN5O2, 308.09. found 308.1.

Sources & evidence

ORD record
ord-6e5c601235624beea3cb92548ba9785b
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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