Methyl iodide → 2,4-dichloro-5,6a-dimethyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

HRID 2386225Notes

Reaction equation

HRID 2386225 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([Cl:12])[C:9]2[N:8]([CH3:13])[C:7](=[O:14])[CH:6]3[CH2:15][O:16][CH2:17][CH2:18][N:5]3[C:4]=2[N:3]=1.IC.[CH3:21]C([O-])(C)C>CS(C)=O.O>[Cl:1][C:2]1[N:11]=[C:10]([Cl:12])[C:9]2[N:8]([CH3:13])[C:7](=[O:14])[C:6]3([CH3:21])[CH2:15][O:16][CH2:17][CH2:18][N:5]3[C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 45749132-Methylpropan-2-olateHCID 866515662,4-dichloro-5-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Product 1

HCID 866515672,4-dichloro-5,6a-dimethyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-oneYield 95.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

2,4-Dichloro-5-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (20 mg, 0.069 mmol) and iodomethane (9.82 mg, 0.069 mmol) were stirred in DMSO (2 mL). The mixture was frozen then 2-methylpropan-2-olate (19.94 mg, 0.208 mmol) was added as a solid followed by a layer of DMSO. The mixture was refrozen then allowed to warm up to room temperature and stirred for 1 hour. The reaction was diluted with water and extracted twice with EtOAc, the organic layers combined, dried over magnesium sulfate, filtered and evaporated in vacuo to give 20 mg (95%) of 2,4-dichloro-5,6a-dimethyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one as a white solid. MS [M+H] Found 303.

Workup

  1. temperatureThe mixture was frozen
  2. extractionextracted twice with EtOAc
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-5f730fe949634ee7934ab23c34c29a86
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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