Methyl iodide → HCID 58181119, compound

HRID 469309Notes

Reaction equation

HRID 469309 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([C:10]([C:12]2[CH:21]=[CH:20][C:15]3[NH:16][C:17](=[O:19])[O:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=1.I[CH3:23]>CN(C=O)C>[Cl:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([C:10]([C:12]2[CH:21]=[CH:20][C:15]3[N:16]([CH3:23])[C:17](=[O:19])[O:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58181175HCID 58181175, compound

Product 1

HCID 58181119HCID 58181119, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

135 mg (3.10 mmol) sodium hydride (55%, suspension in mineral oil) were added to 800 mg (2.90 mmol) 6-(6-chloro-pyrimidine-4-carbonyl)-3H-benzoxazol-2-one in 10 mL DMF and the mixture was stirred for 30 min at RT. Then 0.368 mL (5.80 mmol) iodomethane were added and the mixture was stirred for a further hour at RT. The mixture was mixed with ice water and extracted twice with EtOAc. The organic phases were combined, washed with water, dried and evaporated down. The residue was triturated with DIPE, suction filtered and dried.

Workup

  1. stirringthe mixture was stirred for a further hour at RT
  2. extractionextracted twice with EtOAc
  3. washwashed with water
  4. customdried
  5. customevaporated down
  6. customThe residue was triturated with DIPE, suction
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-f145eed77bf748c7bc2a9c6bd1054dcd
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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