Benzothiazole → (+/-)-6-[1-Hydroxy-1-(benzothiazol-2-yl)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 379571Notes

Reaction equation

HRID 379571 reaction equation
C([N-]C(C)C)(C)C.[Li+].[S:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[CH:10]1.[CH3:18][N:19]1[C:24](=[O:25])[C:23]2[CH:26]=[C:27]([CH:29]=[O:30])[S:28][C:22]=2[N:21]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:20]1=[O:35].C(=O)([O-])O.[Na+]>O1CCCC1>[OH:30][CH:29]([C:27]1[S:28][C:22]2[N:21]([CH2:31][CH:32]([CH3:33])[CH3:34])[C:20](=[O:35])[N:19]([CH3:18])[C:24](=[O:25])[C:23]=2[CH:26]=1)[C:10]1[S:9][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=1

Participants

6

Reactant 4

HCID 7222BenzothiazoleHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamideHCID 183665971,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-6-carboxaldehyde

Product 1

HCID 18366604(+/-)-6-[1-Hydroxy-1-(benzothiazol-2-yl)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 33.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium diisopropylamide (2.25 mmol) was added to a solution of benzothiazole (230 mg) in tetrahydrofuran (10 ml) at −78° C. After 5 minutes 1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-6-carboxaldehyde (300 mg) was added and the reaction mixture kept at −78° C. After a further 30 minutes saturated sodium hydrogen carbonate solution was added and the reaction mixture was allowed to warm to room temperature. The mixture was extracted with ethyl acetate, dried over magnesium sulfate and evaporated. Purification by chromatography eluting with isohexane:ethyl acetate (2:1 to 1:2) gave the title compound as an oil (150 mg).

Workup

  1. customkept at −78° C
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customPurification by chromatography
  6. washeluting with isohexane:ethyl acetate (2:1 to 1:2)

Sources & evidence

ORD record
ord-6c400866bb8145b0ab27c746bb2b4f02
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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