Methyl iodide → HCID 89782132, compound

HRID 1056284Notes

Reaction equation

HRID 1056284 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[S:12])[N:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:7]2=[O:19].[C:20]([O-])([O-])=O.[K+].[K+].CI>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([S:12][CH3:20])[N:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:7]2=[O:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 89783777HCID 89783777, compound

Product 1

HCID 89782132HCID 89782132, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8-bromo-3-(pyridin-2-yl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (330 mg, 0.987 mmol, 415b), K2CO3 (59.6 mg, 0.987 mmol), and THF (9.9 mL) was set stirring under nitrogen at RT. MeI (61.3 pt, 0.987 mmol) was added, and the mixture was set stirring at 75° C. for 4 h. The reaction was cooled to RT and filtered, rinsing with chilled THF. The filtrate was concentrated under reduced pressure to give 310 mg of a waxy yellow-brown solid that contained the product. m/z (ESI, +ve) 349.7 (M+H)+.

Workup

  1. stirringthe mixture was set stirring at 75° C. for 4 h
  2. temperatureThe reaction was cooled to RT
  3. filtrationfiltered
  4. washrinsing with chilled THF
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-795ae40335eb4025b02251855faf7fac
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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