Methyl iodide → HCID 68461181, compound

HRID 501188Notes

Reaction equation

HRID 501188 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[C:14]1[N:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][N:15]=1.[CH3:24]C(C)([O-])C.[K+].CI>CN(C=O)C.CCOC(C)=O>[CH3:24][N:12]1[C:13]2[CH2:1][N:2]([C:14]3[N:15]=[CH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:19]=3)[CH2:3][CH2:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 58703314HCID 58703314, compound

Product 1

HCID 68461181HCID 68461181, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of Example 8 (200 mg, mmol) in DMF (5 mL) was added potassium t-butoxide (145 mg) at 0° C. After stirring the suspension for 10-15 min at 0° C., methyl iodide (0.11 g, mmol) was added. The mixture was stirred at 0° C. for 30 min. and then stirred at room temperature for 3 hours. After completion, the reaction mixture was diluted with EtOAc. The organic layer was separated, washed with saturated sodium bicarbonate, dried over sodium sulfate and concentrated under vacuum. The crude product obtained was purified by column chromatography using EtOAc in hexanes (50%) to obtain methyl 2-(9-methyl-1,3,4,9-tetrahydro-2H-b-carbolin-2-yl)pyrimidine-5-carboxylate (160 mg, 76.5% yield). 1HNMR (DMSO-d6) ppm: 2.8 (t, 2H, CH2); 3.65 (s, 3H, N—CH3); 3.8 (s, 3H, OCH3); 4.2 (t, 2H, CH2); 5.15 (s, 2H, CH2); 7.0-7.2 (m, 2H); 7.4 (d, 2H); 8.8 (s, 2H); m/e=323 (M+1).

Workup

  1. stirringThe mixture was stirred at 0° C. for 30 min.
  2. stirringstirred at room temperature for 3 hours
  3. customThe organic layer was separated
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe crude product obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-dca9a3d2f59744f58c35f2c544aee8f5
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

Loading…