2-(Methylthio)benzothiazole → Methyl 1,2,3,4-tetrahydro-3-methyl-1-(isobutyl)-2,4-dioxo-6-[2-thioxo-3(2H)-benzothiazolylmethyl]thieno[2,3-d]pyrimidine-5-carboxylate

HRID 131567Notes

Reaction equation

HRID 131567 reaction equation
Br[CH2:2][C:3]1[S:18][C:6]2[N:7]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:8](=[O:13])[N:9]([CH3:12])[C:10](=[O:11])[C:5]=2[C:4]=1[C:19]([O:21][CH3:22])=[O:20].C[S:24][C:25]1[S:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[N:29]=1>COCCOCCOC>[CH3:12][N:9]1[C:10](=[O:11])[C:5]2[C:4]([C:19]([O:21][CH3:22])=[O:20])=[C:3]([CH2:2][N:29]3[C:28]4[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=4[S:26][C:25]3=[S:24])[S:18][C:6]=2[N:7]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:8]1=[O:13]

Participants

4

Reactant 2

HCID 119892-(Methylthio)benzothiazoleHCID 16102871Methyl 6-bromomethyl-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

Product 1

HCID 86760683Methyl 1,2,3,4-tetrahydro-3-methyl-1-(isobutyl)-2,4-dioxo-6-[2-thioxo-3(2H)-benzothiazolylmethyl]thieno[2,3-d]pyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of the product of example 3 step b) (300 mg) and 2-methylthiobenzothiazole (300 mg) in diglyme (3 ml) was heated by microwave irradiation (600 W) to 160° C. After 30 min the solvent was removed by vacuum distillation and the residue purified by gradient chromatography eluting with a gradient of dichloromethane to 5% methanol in dichloromethane to give the sub-title compound as a white solid (150 mg). δ 1HCDCl3 0.93 (6H,d), 2.22 (1H,non), 3.38 (3H,s), 3.71 (2H,d), 4.00 (3H,s), 4.80 (2H,s), 7.33 (1H,dt), 7.45 (1H,dt), 7.77 (1H,dd), 7.92 (1H,d).

Workup

  1. customAfter 30 min the solvent was removed by vacuum distillation
  2. customthe residue purified by gradient chromatography
  3. washeluting with a gradient of dichloromethane to 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-efc040ef24b14ec9888f5fc15fe4ea95
Source dataset
uspto-grants-2008_06
Patent number
US07384950B2

Reaction notes

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