2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → 6-Bromo-8-chloro-4-isopropyl-7-ethoxy-2,2-dimethyl-2H-chromene

HRID 2180469Notes

Reaction equation

HRID 2180469 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([Cl:20])[C:16]=1[O:17][CH2:18][CH3:19])[O:13][C:12]([CH3:22])([CH3:21])[CH2:11][C:10]2=O.CN1CCCN(C)C1=O>C1COCC1>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([Cl:20])[C:16]=1[O:17][CH2:18][CH3:19])[O:13][C:12]([CH3:22])([CH3:21])[CH:11]=[C:10]2[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 224907976-Bromo-8-chloro-7-ethoxy-2,2-dimethyl-chroman-4-one2×HCID 178418918HCID 178418918, compound

Product 1

HCID 224909896-Bromo-8-chloro-4-isopropyl-7-ethoxy-2,2-dimethyl-2H-chromene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure C, isopropylmagnesium chloride (2.0 M in THF, 111 mL, 22 mmol), 6-bromo-8-chloro-7-ethoxy-2,2-dimethyl-chroman-4-one (Compound 10, 1.5 g, 4.5 mmol), and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU, 2.6 mL) in THF was reacted then quenched with 10% HCl, and stored at room temperature for 12 h.

Workup

  1. customwas reacted
  2. customthen quenched with 10% HCl

Sources & evidence

ORD record
ord-a03f70e9cd574531a1f5a9486abaecd6
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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