Methyl iodide → HCID 86651581, compound

HRID 2386256Notes

Reaction equation

HRID 2386256 reaction equation
[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])[C@H:6]3[CH2:17][O:18][CH:19]([CH3:21])[CH2:20][N:5]3[C:4]=2[N:3]=1.IC.[CH3:24]C([O-])(C)C.[Na+]>CS(C)=O>[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([CH3:24])[CH2:17][O:18][CH:19]([CH3:21])[CH2:20][N:5]3[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23676156Sodium t-butoxideHCID 86651579HCID 86651579, compound

Product 1

HCID 86651581HCID 86651581, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
0 °C

Procedure

To (R)-2-chloro-5-(cyclopropylmethyl)-9-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (124 mg, crude) was added iodomethane (0.25 mL, 4 mmol) and DMSO (2 mL). The mixture was cooled to 0° C. and then −78° C. and sodium 2-methylpropan-2-olate (0.154 g, 1.6 mmol) was added, followed by more DMSO (0.7 mL). The cooling bath was removed and the mixture was stirred at room temperature for 14 hours and then diluted with EtOAc and water, extracted with EtOAc and dried over Na2SO4. Solvent was removed to give crude (R)-2-chloro-5-(cyclopropylmethyl)-6a,9-dimethyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one. MS [M+H] found 323.3.

Workup

  1. customThe cooling bath was removed
  2. additiondiluted with EtOAc and water
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customSolvent was removed

Sources & evidence

ORD record
ord-dfe278a986914544ba31cad3ef395166
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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