2-Propanethiol → 1,2,3,4-Tetrahydro-3-methyl-5-[(1-methylethyl)thio]-1-(2-methylpropyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-6-carboxaldehyde

HRID 379598Notes

Reaction equation

HRID 379598 reaction equation
Cl[C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]=2[S:4][C:3]=1[CH:18]=[O:19].[H-].[Na+].[CH3:22][CH:23]([SH:25])[CH3:24]>CN(C)C=O.O>[CH3:12][N:8]1[C:9](=[O:11])[C:10]2[C:2]([S:25][CH:23]([CH3:24])[CH3:22])=[C:3]([CH:18]=[O:19])[S:4][C:5]=2[N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7]1=[O:13]

Participants

6

Reactant 3

HCID 63642-PropanethiolHCID 24758Sodium hydrideHCID 183666245-Chloro-1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-6-carboxaldehyde

Product 1

HCID 183665731,2,3,4-Tetrahydro-3-methyl-5-[(1-methylethyl)thio]-1-(2-methylpropyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-6-carboxaldehydeYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-thieno[2,3-d]pyrinidine-6-carboxaldehyde (Example 50 step b; 2 g) in dimethylformamide (20 ml) was added sodium hydride (0.3 g of 60% dispersion) followed by the addition of 2-propanethiol (0.6 g). The mixture was stirred for 24 hours at ambient temperature then the reaction was diluted with water (100 ml) and extracted thrice with ethyl acetate (3×100 ml). The organic phase was washed with water (100 ml), then with brine (100 ml) and then dried, filtered and evaporated to leave the subtitle compound as a pale yellow solid (2.24 g).

Workup

  1. extractionextracted thrice with ethyl acetate (3×100 ml)
  2. washThe organic phase was washed with water (100 ml)
  3. dry with materialwith brine (100 ml) and then dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ee48071423314e6bbafcef12c00251a2
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

Loading…