3-(7-Hydroxy-2,4-dimethoxy-5,5-dimethyl-5,7-dihydro-furo[3,4-d]pyrimidin-7-yl)-5-methyl-benzonitrile → 3-(7-Hydroxy-5,5-dimethyl-2,4-dioxo-1,2,3,4,5,7-hexahydro-furo[3,4-d]pyrimidin-7-yl)-5-methyl-benzonitrile

HRID 426284Notes

Reaction equation

HRID 426284 reaction equation
[OH:1][C:2]1([C:17]2[CH:18]=[C:19]([CH:22]=[C:23]([CH3:25])[CH:24]=2)[C:20]#[N:21])[C:6]2[N:7]=[C:8]([O:13]C)[N:9]=[C:10]([O:11]C)[C:5]=2[C:4]([CH3:16])([CH3:15])[O:3]1>C(Br)(=O)C>[OH:1][C:2]1([C:17]2[CH:18]=[C:19]([CH:22]=[C:23]([CH3:25])[CH:24]=2)[C:20]#[N:21])[C:6]2[NH:7][C:8](=[O:13])[NH:9][C:10](=[O:11])[C:5]=2[C:4]([CH3:15])([CH3:16])[O:3]1

Participants

3

Reactant 1

HCID 591846603-(7-Hydroxy-2,4-dimethoxy-5,5-dimethyl-5,7-dihydro-furo[3,4-d]pyrimidin-7-yl)-5-methyl-benzonitrile

Product 1

HCID 591848543-(7-Hydroxy-5,5-dimethyl-2,4-dioxo-1,2,3,4,5,7-hexahydro-furo[3,4-d]pyrimidin-7-yl)-5-methyl-benzonitrileYield 25.1%

Reagents, catalysts & solvents 1

HCID 10482Acetyl bromideSolvent

Procedure

A solution of 3-(7-Hydroxy-2,4-dimethoxy-5,5-dimethyl-5,7-dihydro-furo[3,4-d]pyrimidin-7-yl)-5-methyl-benzonitrile (0.027 g, 0.080 mmol) in acetyl bromide (2.0 mL) was heated at 60° C. for 3 h. Reaction mixture was concentrated and purified by reverse phase HPLC (Phenomenex Synergi® column, 5 to 100% acetonitrile/H2O) to give a desired product (0.0063 g, 25%). 1H NMR (300 MHz, CD3OD): δ 7.76 (s, 1H), 7.70 (s, 1H), 7.51 (s, 1H), 2.38 (s, 1H), 1.60 (s, 3H), 1.59 (s, 3H). Mass spectrum: 314.0 (M+H)+.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. custompurified by reverse phase HPLC (Phenomenex Synergi® column, 5 to 100% acetonitrile/H2O)

Sources & evidence

ORD record
ord-2235f037b51348149d1e79891357672f
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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