Sodium methanethiolate → HCID 118598804, compound

HRID 1050345Notes

Reaction equation

HRID 1050345 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[C:5](=[O:15])[N:4]2[C:16]([CH3:21])([CH3:20])[NH:17][C:18](=[O:19])[C:3]=12.[CH3:22][S-:23].[Na+]>CN(C)C=O>[CH3:20][C:16]1([CH3:21])[N:4]2[C:5](=[O:15])[C:6]([NH:8][C:9]3[CH:14]=[CH:13][N:12]=[CH:11][N:10]=3)=[CH:7][C:2]([S:23][CH3:22])=[C:3]2[C:18](=[O:19])[NH:17]1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 118598634HCID 118598634, compound

Product 1

HCID 118598804HCID 118598804, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a vial was added 8-chloro-3,3-dimethyl-6-(pyrimidin-4-ylamino)-2H-imidazo[1,5-c]pyridine-1,5-dione (1, 0.30 g, 0.98 mmol) in dimethylformamide (5 mL). Sodium thiomethoxide (0.14 g, 1.96 mmol) was added at room temperature, the vial was sealed and heated at 110° C. for 36 h. The reaction mixture was quenched with an aqueous ammonium chloride solution and extracted with 10% methanol in dichloromethane. The organic layers were separated, combined, dried over sodium sulfate, filtered and concentrated it to dryness. Solids were precipitated by the addition of ice, filtered and dried. The solid material was subjected to preparative HPLC to afford 3,3-dimethyl-8-methylsulfanyl-6-(pyrimidin-4-ylamino)-2H-imidazo[1,5-a]pyridine-1,5-dione (Cpd. No. 82) as a yellow solid. Yield: 0.060 g, 19%; MS (ESI) m/z 318.42 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 10.02 (s, 1H), 9.66 (s, 1H), 8.92 (s, 1H), 8.84 (s, 1H), 8.45 (d, J=6.0 Hz, 1H), 7.47 (d, J=6.4 Hz, 1H), 2.47 (s, 3H), 1.80 (s, 6H).

Workup

  1. customthe vial was sealed
  2. customThe reaction mixture was quenched with an aqueous ammonium chloride solution
  3. extractionextracted with 10% methanol in dichloromethane
  4. customThe organic layers were separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated it to dryness
  8. customSolids were precipitated by the addition of ice
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-7be847bb908c46659de849437b36b463
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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