1,2,4-Triazine, 3,5-bis[(trimethylsilyl)oxy]- → 2,4-Bis(tetrahydro-2-pyranyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine

HRID 848636Notes

Reaction equation

HRID 848636 reaction equation
C[Si](C)(C)[O:3][C:4]1[N:5]=[N:6][CH:7]=[C:8]([O:10][Si](C)(C)C)[N:9]=1.Cl[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1>CN(C)C=O>[O:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH:18]1[N:5]1[C:4](=[O:3])[N:9]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C:8](=[O:10])[CH:7]=[N:6]1

Participants

4

Reactant 2

HCID 870571,2,4-Triazine, 3,5-bis[(trimethylsilyl)oxy]-HCID 5244002-Chlorooxane

Product 1

HCID 127800582,4-Bis(tetrahydro-2-pyranyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazineYield 47.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,5-Bis(trimethylsilyloxy)-1,2,4-triazine (2.5 g) and 2-chlorotetrahydropyran (1.8 g) are dissolved in dimethylformamide (1 ml), and the mixture is stirred overnight at room temperature and concentrated in vacuo. The residue is column-chromatographed over silica gel using a mixture of acetone/n-hexane (1/3) as an eluent. The first major fraction gives 1.0 g (40%) of 2,4-bis(tetrahydro-2-pyranyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (Compound No. 87) (yield, 1.0 g; 36%), the second gives 4-(tetrahydro-2-pyranyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (Compound No. 88) (yield, 0.8 g; 40%) and the third gives 2-(tetrahydro-2-pyranyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (Compound No. 100) (yield, 0.6 g; 30%). Compound Nos. 87 and 88 melt at 32° C. and 116° C., respectively.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is column-chromatographed over silica gel using
  3. additiona mixture of acetone/n-hexane (1/3) as an eluent

Sources & evidence

ORD record
ord-dc0f92aaa36443ad9beeea8d601fede7
Source dataset
uspto-grants-1981_10
Patent number
US04297129

Reaction notes

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