Methyl iodide → HCID 86651588, compound

HRID 1696025Notes

Reaction equation

HRID 1696025 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]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.[CH3:23]C(C)([O-])C.[Na+].IC>CS(C)=O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[C:7](=[O:18])[C:6]3([CH3:23])[CH2:19][O:20][CH2:21][CH2:22][N:5]3[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23676156Sodium t-butoxideHCID 86651587HCID 86651587, compound

Product 1

HCID 86651588HCID 86651588, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a 20 mL vial containing 2-chloro-5-(tetrahydro-2H-pyran-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (0.0907 g, 0.279 mmol) was added DMSO (0.5 mL); placed in a dry ice-acetone bath and then added sodium tert-butoxide (0.030 g, 0.307 mmol) followed by DMSO (0.5 mL) and iodomethane (0.019 ml, 0.307 mmol). The dry ice-acetone bath was removed and the mixture was allowed to warm up to room temperature and stirred for 16 h. The reaction was diluted with 10 mL of water and vigorously stirred at room temperature. Collected rust/orange solids by vacuum filtration, washed with additional water and dried under high vacuum affording 2-chloro-6a-methyl-5-(tetrahydro-2H-pyran-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (46.0 mg, 48.4% yield) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.41 (d, J=0.76 Hz, 3 H) 2.48-2.72 (m, 2 H) 3.17-3.34 (m, 1 H) 3.41-3.77 (m, 5 H) 3.94-4.19 (m, 6 H) 4.61 (tt, J=12.38, 4.29 Hz, 1H) 7.98-8.14 (m, 1 H). MS [M+H] found 339.3.

Workup

  1. customplaced in a dry ice-acetone bath
  2. customThe dry ice-acetone bath was removed
  3. additionThe reaction was diluted with 10 mL of water
  4. stirringvigorously stirred at room temperature
  5. filtrationCollected rust/orange solids by vacuum filtration
  6. washwashed with additional water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-180b63ade1d345c8b8ee95a1712de887
Source dataset
uspto-grants-2012_04
Patent number
US08163755B2

Reaction notes

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