Sodium hydride → Trifluoroacetic acid

HRID 920377Notes

Reaction equation

HRID 920377 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH2:12][OH:13])[CH:7]=[C:8]([F:11])[C:9]=1[F:10].[F:14][C:15]([F:20])([F:19])[C:16]([OH:18])=[O:17].Cl[C:22]1[CH:32]=[C:26]2[N:27]([CH3:31])[CH2:28][CH2:29][CH2:30][N:25]2[C:24](=[O:33])[N:23]=1>CN(C=O)C>[CH3:31][N:27]1[CH2:28][CH2:29][CH2:30][N:25]2[C:24](=[O:33])[N:23]=[C:22]([O:13][CH2:12][C:6]3[CH:5]=[C:4]([F:3])[C:9]([F:10])=[C:8]([F:11])[CH:7]=3)[CH:32]=[C:26]12.[C:16]([OH:18])([C:15]([F:20])([F:19])[F:14])=[O:17]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27770403,4,5-Trifluorobenzyl alcoholHCID 86676392HCID 86676392, compound

Product 2

HCID 6422Trifluoroacetic acidYield 11.42%HCID 71236712HCID 71236712, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of NaH (38.3 mg, 0.956 mmol) in DMF (2 mL) was added (3,4,5-trifluorophenyl)methanol (65 mg, 0.401 mmol) at rt. The reaction mixture was stirred for 5 mins at rt, and then 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one trifluoroacetic acid salt (100 mg, 0.319 mmol) was added. The reaction mixture was stirred for another 1 h at rt, quenched with water and then filtered to give clear solution. The solution was purified by MDAP (0.3% TFA in water/MeCN) to afford the title compound as its TFA salt (16 mg, 0.036 mmol, 11.42%).

Workup

  1. stirringThe reaction mixture was stirred for another 1 h at rt
  2. customquenched with water
  3. filtrationfiltered
  4. customto give clear solution
  5. customThe solution was purified by MDAP (0.3% TFA in water/MeCN)

Sources & evidence

ORD record
ord-b0dd83b5ba854cc2b7df1f05e94c5839
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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