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

HRID 2180468Notes

Reaction equation

HRID 2180468 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:19])[C:16]=1[O:17][CH3:18])[O:13][C:12]([CH3:21])([CH3:20])[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:19])[C:16]=1[O:17][CH3:18])[O:13][C:12]([CH3:21])([CH3:20])[CH:11]=[C:10]2[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 224910326-Bromo-8-chloro-7-methoxy-2,2-dimethyl-chroman-4-one2×HCID 178418918HCID 178418918, compound

Product 1

HCID 224908856-Bromo-8-chloro-4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure C, isopropylmagnesium chloride (2.0 M in THF, 3.15 mL, 6.29 mmol), 6-bromo-8-chloro-7-methoxy-2,2-dimethyl-chroman-4-one (Compound 9, 400 mg, 1.26 mmol) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 2 mL) in THF was reacted then quenched with 10% HCl, and stored at room temperature for 12 h. Purification by flash chromatography (silica gel, 95:5 hexane/ethyl acetate) afforded the title compound as a yellow oil.

Workup

  1. customwas reacted
  2. customthen quenched with 10% HCl
  3. customPurification by flash chromatography (silica gel, 95:5 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f4d7f6c7b355454588375302e5753934
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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