4-(4-Chloro-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl)-benzoic acid tert-butyl ester → HCID 86591416, compound

HRID 1373051Notes

Reaction equation

HRID 1373051 reaction equation
[C:1]([O:5][C:6](=[O:24])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:19](=[O:20])[C:18]([CH3:21])=[C:17](Cl)[NH:16][C:15]2=[O:23])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[SH2:25].[Na]>CN(C)C=O>[C:1]([O:5][C:6](=[O:24])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:19](=[O:20])[C:18]([CH3:21])=[C:17]([SH:25])[NH:16][C:15]2=[O:23])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 693740034-(4-Chloro-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl)-benzoic acid tert-butyl esterHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 86591416HCID 86591416, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The product of Example 1, Step (A) (0.54 g) was dissolved in dimethylformamide (5 mL) wand treated with sodium hydrogen sulfide (0.29 g) and heated at 60° C. for 18 hours. The solvent was removed in a vacuum and the residue stirred with 1 M hydrochloric acid (15 mL) for 1 hour. The resulting solid was filtered, rinsed with water and dried in a vacuum at room temperature to give 4-(4-mercapto-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl)-benzoic acid tert-butyl ester (0.475 g, 91% yield). 1H-NMR (DMSO-d6) δ 10.99 (s), 7.76(d, 2H), 7.27 (d, 2H), 5.52 (s, 2H), 1.91, (s, 3H), 1.50 (s, 9H).

Workup

  1. customThe solvent was removed in a vacuum
  2. filtrationThe resulting solid was filtered
  3. washrinsed with water
  4. customdried in a vacuum at room temperature

Sources & evidence

ORD record
ord-18121205ad204ae297df891c60163a0b
Source dataset
uspto-grants-2007_01
Patent number
US07160893B2

Reaction notes

Loading…