Methyl iodide → HCID 67324990, compound

HRID 1716389Notes

Reaction equation

HRID 1716389 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:29])[NH:9][C:10]1[S:11][C:12]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]3[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=3)[N:16]=2)=[CH:13][CH:14]=1)([CH3:6])([CH3:5])[CH3:4].[CH3:30]I>C1COCC1>[C:3]([O:7][C:8](=[O:29])[N:9]([CH3:30])[C:10]1[S:11][C:12]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]3[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=3)[N:16]=2)=[CH:13][CH:14]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 59468607HCID 59468607, compound

Product 1

HCID 67324990HCID 67324990, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% disersion in mineral oil) (21.4 mg, 0.535 mmol) was added to a solution of [5-(2-m-tolylamino-pyrimidin-4-yl)-thiophen-2-yl]-carbamic acid tert-butyl ester (186 mg, 0.486 mmol) in anhydrous THF (5 mL) at ice bath temperature. After 15 minutes, MeI was added and the mixture was removed from the ice bath. Additional NaH (7.7 mg, 0.19 mmol) and MeI (9.0 uL, 0.145 mmol) were added after 5 hours and the reaction was stirred 3 days. The reaction was quenched by addition of a few drops of water and was concentrated to dryness and taken to the next step without further purification. MS: m/z 397 (M+H+).

Workup

  1. customthe mixture was removed from the ice bath
  2. customThe reaction was quenched by addition of a few drops of water
  3. concentrationwas concentrated to dryness
  4. customtaken to the next step without further purification

Sources & evidence

ORD record
ord-920627a8e76c4bca9deab596f99207b9
Source dataset
uspto-grants-2010_09
Patent number
US07803806B2

Reaction notes

Loading…