Methyl iodide → HCID 86651564, compound

HRID 1695980Notes

Reaction equation

HRID 1695980 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]3[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=3)[C:7](=[O:19])[CH:6]3[CH2:20][O:21][CH2:22][CH2:23][N:5]3[C:4]=2[N:3]=1.IC.[CH3:26]C([O-])(C)C.[Na+]>CS(C)=O.O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]3[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=3)[C:7](=[O:19])[C:6]3([CH3:26])[CH2:20][O:21][CH2:22][CH2:23][N:5]3[C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 23676156Sodium t-butoxideHCID 866515632-chloro-5-((1-methyl-1H-pyrazol-3-yl)methyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Product 1

HCID 86651564HCID 86651564, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

2-Chloro-5-((1-methyl-1H-pyrazol-3-yl)methyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (100 mg, 0.299 mmol) and iodomethane (0.037 mL, 0.597 mmol) were mixed in DMSO (2 mL) in a sealed scintillation vial. The mixture was frozen then sodium 2-methylpropan-2-olate (57.4 mg, 0.597 mmol) was added and covered with a layer of DMSO. The mixture was refrozen then allowed to warm to room temperature and stirred overnight. An additional 1 eq of iodomethane was added. After 1 hour the reaction was diluted with water and extracted into EtOAc. The organic layer was dried over magnesium sulfate, filtered, and evaporated in vacuo to give 2-chloro-6a-methyl-5-((1-methyl-1H-pyrazol-3-yl)methyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one as a yellow oil, which was used without further purification. MS [M+H] Found 349.

Workup

  1. temperatureThe mixture was frozen
  2. extractionextracted into EtOAc
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-26161a891e914fe7a3c39c2f14feece6
Source dataset
uspto-grants-2012_04
Patent number
US08163755B2

Reaction notes

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