[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][CH:13]3[CH2:15][CH2:14]3)[C:7](=[O:16])[CH:6]3[CH2:17][O:18][CH2:19][CH2:20][N:5]3[C:4]=2[N:3]=1.IC.[CH3:23]C(C)([O-])C.[Na+]>CS(C)=O.O.ClCCl>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][CH:13]3[CH2:14][CH2:15]3)[C:7](=[O:16])[C:6]3([CH3:23])[CH2:17][O:18][CH2:19][CH2:20][N:5]3[C:4]=2[N:3]=1To 2-chloro-5-(cyclopropylmethyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (3.57 g, 12.11 mmol) in DMSO (28 mL) was added iodomethane (0.907 mL, 14.54 mmol), and the mixture was cooled in an ice-water bath. Then sodium tert-butoxide (1.39 g, 14.54 mmol) was added. After 5 minutes stirring at 0° C., the mixture was allowed to warm up to room temperature and stirred for 17 hours. The reaction mixture was cooled in an ice-water bath and more iodomethane (0.378 mL) was added, followed by more sodium tert-butoxide (582 mg). The mixture was warmed up to room temperature and stirred for 55 minutes, then sealed and heated at 50° C. (bath temperature) for 1 hour. The reaction was cooled to room temperature and additional iodomethane (3 mL) was added, then sealed and heated at 50° C. (bath temperature) for another 27 minutes then cooled in an ice-water bath and more sodium tert-butoxide (582 mg) was added. The mixture was then warmed up to room temperature and stirred for 75 minutes. The reaction mixture was then diluted with water and extracted with EtOAc. The organic layers were combined and solvent was removed to give a brown solid. The solid was dissolved in dichloromethane and purified on silica gel eluting with Hexanes-EtOAc (0-50%), to give 2-chloro-5-(cyclopropylmethyl)-6a-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one as a solid (773 mg, 33%). MS [M+H] found 309.2.
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