Pyrimidine → 4-(3-Methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 1721623Notes

Reaction equation

HRID 1721623 reaction equation
ClC[N:3]1[C:7](=[O:8])[CH:6]([CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[N:5]([CH3:14])[S:4]1(=[O:16])=[O:15].N1C=CC=NC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:12][CH:11]([CH3:13])[CH2:10][CH2:9][CH:6]1[N:5]([CH3:14])[S:4](=[O:16])(=[O:15])[NH:3][C:7]1=[O:8]

Participants

5

Reactant 3

HCID 9260PyrimidineHCID 11430Potassium CarbonateHCID 15817425HCID 15817425, compound

Product 1

HCID 189222624-(3-Methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloromethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (1 g; 3.72 mmol), 2,4-dioxo-4-H-pyrido 1,2-a!pyrimidine (Formula IV: X=H; Y= ##STR18## (0.72 g; 4.44 mmol), and potassium carbonate (0.67 g; 4.84 mmol) in 35 ml of DMF was stirred at room temperature for 24 hours. The mixture was poured into ice/water, extracted with ethyl acetate, and the organic layer was washed with water, brine, and dried. The solvent was concentrated in vacuo and the residue purified by silica gel flash chromatography (70% hexane/ethyl acetate, 5% methanol/ethyl acetate) to afford 0.29 g of 2-(4-oxo-4-H-pyrido 1,2-a!pyrimidin-2-yl-oxymethyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: R1 =H; R2 =(CH2)2CH(CH3); R3 =CH3 ; ##STR19## Example 1J) as a solid, m.p. 106.5°-107.5° C., and 0.34 g of 2-(4-oxo-4-H-2-hydroxypyrido 1,2-a!pyrimidin-3-yl-methyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide as a solid, m.p. 165°-170° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed with water, brine
  3. customdried
  4. concentrationThe solvent was concentrated in vacuo
  5. customthe residue purified by silica gel flash chromatography (70% hexane/ethyl acetate, 5% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-d75188b20ab94f588ce97f251cd956a6
Source dataset
uspto-grants-1996_04
Patent number
US05512576

Reaction notes

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