Methanol → HCID 53251472, compound

HRID 509625Notes

Reaction equation

HRID 509625 reaction equation
O[C:2]([C:4]([F:7])(F)F)=O.[CH3:8][C:9]1[N:14]2[CH:15]=[C:16]([CH2:18][CH2:19][C:20]3[NH:21][CH:22]=[C:23]([C:25]4[S:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[N:17]=[C:13]2[N:12]=[C:11]([CH3:30])[CH:10]=1.[H-].[Na+].BrCCF.CO>CN(C=O)C>[F:7][CH2:4][CH2:2][N:21]1[CH:22]=[C:23]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[C:20]1[CH2:19][CH2:18][C:16]1[N:17]=[C:13]2[N:12]=[C:11]([CH3:30])[CH:10]=[C:9]([CH3:8])[N:14]2[CH:15]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 129822-Fluoroethyl bromideHCID 24758Sodium hydrideHCID 178426228HCID 178426228, compound

Product 1

HCID 53251472HCID 53251472, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5,7-Dimethyl-2-[2-(4-thiophen-2-yl-1H-imidazol-2-yl)-ethyl]-imidazo[1,2-a]pyrimidine TFA salt (10.9 mg, 0.025 mmol) in DMF (6 mL) was added sodium hydride (60% in mineral oil, 7.0 mg, 0.175 mmol), the reaction vessel was capped and stirred at RT for 5 minutes. 1-Bromo-2-fluoroethane (4.76 mg, 0.0375 mmol) was added and the reaction was shaken under an atmosphere of argon for 30 minutes at RT then 30 minutes at 70° C. To the cooled reaction methanol (100 μL) was added and the solution subjected to preparative LC-MS purification to yield the title compound. 39% yield, LC-MS: m/z=370.2 (MH+), tR=0.43 minutes, method A.

Workup

  1. customthe reaction vessel was capped
  2. stirringthe reaction was shaken under an atmosphere of argon for 30 minutes at RT
  3. custom30 minutes
  4. customat 70° C
  5. additionwas added
  6. customthe solution subjected to preparative LC-MS purification

Sources & evidence

ORD record
ord-f6f5623717af4d33a6966a603c2333b4
Source dataset
uspto-grants-2015_08
Patent number
US09096589B2

Reaction notes

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