Ethyl Acetate → Methyl 6-(bromomethyl)-1-isopropyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

HRID 131575Notes

Reaction equation

HRID 131575 reaction equation
OC1CON(C([C:9]2[C:17]3[C:16](=[O:18])[N:15]([CH3:19])[C:14](=[O:20])[N:13]([CH:21]([CH3:23])[CH3:22])[C:12]=3[S:11][C:10]=2CC2C3C(=NC=CC=3)NC=2)=O)C1.[Br:34]N1C(=O)CCC1=O.[C:42]([O:45][CH2:46]C)(=[O:44])[CH3:43]>>[Br:34][CH2:9][C:10]1[S:11][C:12]2[N:13]([CH:21]([CH3:23])[CH3:22])[C:14](=[O:20])[N:15]([CH3:19])[C:16](=[O:18])[C:17]=2[C:43]=1[C:42]([O:45][CH3:46])=[O:44]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 688045155-[[4-Hydroxyisoxazolidin-2-yl]carbonyl]-3-methyl-1-(1-methylethyl)-6-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 68806593Methyl 6-(bromomethyl)-1-isopropyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

Procedure

A solution of the product of example 8, part b), (1.6 g), N-bromosuccinimide (1 g), and azoisobutyronitrile (10 mg) in ethyl acetate (25 ml) was refluxed for 1 h. The solution was cooled to room temperature, washed successively with dilute sodium hydroxide solution and water, the organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with diethyl ether/i-hexane (1:1) to give the sub-title compound as a solid (1.5 g). δ 1HCDCl3 1.62 (6H, d), 3.37 (3H, s), 3.99 (3H, s), 3.60-3.70 (3H, m)

Workup

  1. washwashed successively with dilute sodium hydroxide solution and water
  2. dry with materialthe organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography over silica
  6. washeluting with diethyl ether/i-hexane (1:1)

Sources & evidence

ORD record
ord-994d91ccabf24a9196d60c7d5ed6ddd0
Source dataset
uspto-grants-2008_06
Patent number
US07384950B2

Reaction notes

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