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

HRID 379569
Notes
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Reaction equation

HRID 379569 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][N:10]1[C:15](=[O:16])[C:14]2[CH:17]=[CH:18][S:19][C:13]=2[N:12]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:11]1=[O:24].[CH3:25][N:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1[CH:35]=[O:36]>O1CCCC1>[OH:36][CH:35]([C:18]1[S:19][C:13]2[N:12]([CH2:20][CH:21]([CH3:22])[CH3:23])[C:11](=[O:24])[N:10]([CH3:9])[C:15](=[O:16])[C:14]=2[CH:17]=1)[C:27]1[N:26]([CH3:25])[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7620841-methyl-1H-1,3-benzodiazole-2-carbaldehydeHCID 2724682Lithium diisopropylamideHCID 52825273-Methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 9930755(+/-)-6-[1-Hydroxy-1-(1-methyl-1H-benzimidazol-2-yl)methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 15.5%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

A solution of lithium diisopropylamide (3.15 mmol) in anhydrous tetrahydrofuran (5 ml) was added to a solution of 3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (500 mg) in anhydrous tetrahydrofuran (20 ml) at −78° C. After 10 minutes, 1-methylbenzimidazole-2-carboxaldehyde (600 mg) was added and the resultant solution kept at −78° C. for 1 hour. The reaction mixture was allowed to warm to ambient temperature and quenched with saturated sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate and washed with saturated sodium hydrogen carbonate and then brine, then dried over a mixture of magnesium sulfate and silica, filtered, and evaporated. Purification by HPLC over silica eluting with an isohexane:ethyl acetate gradient (4:1 to 0:1) gave the title compound (0.13 g).

Workup

  1. customquenched with saturated sodium hydrogen carbonate solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated sodium hydrogen carbonate
  4. dry with materialbrine, then dried over a mixture of magnesium sulfate and silica
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by HPLC over silica eluting with an isohexane

Sources & evidence

ORD record
ord-a42dadee039c4c8cab9e92fadd8430e2
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06300334B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes