Methyl iodide → HCID 86651604, compound

HRID 2386289Notes

Reaction equation

HRID 2386289 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][CH:13]3[CH2:17][CH2:16][O:15][CH2:14]3)[C:7](=[O:18])[CH:6]3[CH2:19][O:20][CH2:21][CH2:22][N:5]3[C:4]=2[N:3]=1.IC.[CH3:25]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][CH:13]3[CH2:17][CH2:16][O:15][CH2:14]3)[C:7](=[O:18])[C:6]3([CH3:25])[CH2:19][O:20][CH2:21][CH2:22][N:5]3[C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23676156Sodium t-butoxideHCID 86651603HCID 86651603, compound

Product 1

HCID 86651604HCID 86651604, compoundYield 116.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

2-Chloro-5-((tetrahydrofuran-3-yl)methyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (320 mg, 0.985 mmol) and iodomethane (0.307 ml, 4.93 mmol) were frozen in DMSO (2 ml). Sodium 2-methylpropan-2-olate (284 mg, 2.96 mmol) was added and covered by a layer of DMSO. The mixture was allowed to warm to room temperature and stir for 1 hour, then was diluted with water then extracted twice with EtOAc. The organic layers were combined, dried over magnesium sulfate, filtered, and evaporated in vacuo to give 390 mg of 2-chloro-6a-methyl-5-((tetrahydrofuran-3-yl)methyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one as a tan oil. [M+H] found 339.

Workup

  1. extractionthen extracted twice with EtOAc
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-cc8f215f17f447c0a259578b90724af9
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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