Trifluoroacetic acid → 2-Hydroxy-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-3-(1H-1,2,3,4-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1828535Notes

Reaction equation

HRID 1828535 reaction equation
[OH:1][C:2]1[N:3]=[C:4]2[CH:26]=[C:25]([CH2:27][CH2:28][C:29]3[S:30][CH:31]=[C:32]([CH:34]([CH3:36])[CH3:35])[N:33]=3)[CH:24]=[CH:23][N:5]2[C:6](=[O:22])[C:7]=1[C:8]1[N:9]=[N:10][N:11](CC2C=CC(OC)=CC=2)[N:12]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[OH:1][C:2]1[N:3]=[C:4]2[CH:26]=[C:25]([CH2:27][CH2:28][C:29]3[S:30][CH:31]=[C:32]([CH:34]([CH3:36])[CH3:35])[N:33]=3)[CH:24]=[CH:23][N:5]2[C:6](=[O:22])[C:7]=1[C:8]1[NH:9][N:10]=[N:11][N:12]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 135724437HCID 135724437, compound

Product 1

HCID 1784398052-Hydroxy-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-3-(1H-1,2,3,4-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-oneYield 65.7%

Procedure

2-Hydroxy-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-3-[2-(4-methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]-4H-pyrido[1,2-a]pyrimidin-4-one (30 mg) was added with anisole (0.15 ml) and trifluoroacetic acid (1 ml) and stirred at room temperature for 20 hours. After the solvent was evaporated under reduced pressure, the residue was added with methanol and toluene and the solvents were evaporated again under reduced pressure. The residue was added with methanol and methylene chloride, and the deposited crystals were collected by filtration to obtain the title compound (15 mg).

Workup

  1. customAfter the solvent was evaporated under reduced pressure
  2. additionthe residue was added with methanol and toluene
  3. customthe solvents were evaporated again under reduced pressure
  4. additionThe residue was added with methanol and methylene chloride
  5. filtrationthe deposited crystals were collected by filtration

Sources & evidence

ORD record
ord-1038f075a512485ead6b45b45f406cc7
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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