Water → 6-(3-Imino-1,3-dihydro-benzo[c]furan-1-yl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 567917

Reaction equation

HRID 567917 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][S:11][C:5]=2[N:4]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:3]1=[O:16].C([N-]C(C)C)(C)C.[Li+].[C:25]([C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH:29]=[O:30])#[N:26].O>O1CCCC1>[NH:26]=[C:25]1[O:30][CH:29]([C:10]2[S:11][C:5]3[N:4]([CH2:12][CH:13]([CH3:14])[CH3:15])[C:3](=[O:16])[N:2]([CH3:1])[C:7](=[O:8])[C:6]=3[CH:9]=2)[C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 1012092-CyanobenzaldehydeHCID 2724682Lithium diisopropylamideHCID 52825273-Methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 222580436-(3-Imino-1,3-dihydro-benzo[c]furan-1-yl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidin-2,4(1H,3H)-dione (500 mg) in tetrahydrofuran (10 ml) at −78° C. was added lithium diisopropylamide (1M, 3.1 ml). After 5 minutes a solution of o-cyanobenzaldehyde in tetrahydrofuran (2 ml) was added and the reaction was allowed to stir for 2 h. Water (10 ml) was the added and the mixture was allowed to warm to room temperature. The mixture was extracted with ethyl acetate. The organic layer was separated and dried over magnesium sulfate, then concentrated in vacuo and purified by normal phase HPLC to yield the title compound (15 mg).

Workup

  1. additionadded
  2. extractionThe mixture was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by normal phase HPLC

Sources & evidence

ORD record
ord-998a81851c3e4775950226110ecde8a5
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Linked notes

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