4-Bromoanisole → HCID 13304949, compound

HRID 280088Notes

Reaction equation

HRID 280088 reaction equation
[Mg:1].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[CH2:11]([C:13]1[C:14]([O:25][CH3:26])=[N:15][C:16]2[N:17]([CH:20]=[C:21]([CH:23]=[O:24])[N:22]=2)[C:18]=1[CH3:19])[CH3:12].[Cl-].[NH4+].O1[CH2:33][CH2:32]CC1>>[CH3:26][O:25][C:14]1[CH:13]=[CH:18][C:19]([Mg:1][Br:2])=[CH:33][CH:32]=1.[CH2:11]([C:13]1[C:14]([O:25][CH3:26])=[N:15][C:16]2[N:17]([CH:20]=[C:21]([CH:23]([C:3]3[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=3)[OH:24])[N:22]=2)[C:18]=1[CH3:19])[CH3:12]

Participants

7

Reactant 5

HCID 77304-BromoanisoleHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 13304948HCID 13304948, compound

Product 2

HCID 13304949HCID 13304949, compoundYield 94%HCID 178491912HCID 178491912, compound

Procedure

A solution of 4-methoxyphenylmagnesium bromide was prepared by treating 0.54 g (22.5 mg-atoms) of magnesium turnings with 4.20 g (22.5 mmol) of p-bromoanisole in 25 ml of dry tetrahydrofuran and was added dropwise to a stirred solution of 1.64 g (7.5 mmol) of 6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-carboxaldehyde in 100 ml of dry tetrahydrofuran. After stirring at room temperature for 1 hour the mixture was poured into saturated ammonium chloride solution and the organic layer was separated. The aqueous layer was extracted with chloroform and the combined organic extracts were dried over MgSO4 and evaporated to dryness under reduced pressure. The residue was deposited on a column of 250 g of silica gel and elution with a 7:3 chloroform-ethyl acetate mixture gave 2.3 g (94% yield) of (6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidin-2-yl)(4-methoxyphenyl)methanol as a white crystalline solid melting at 117°-9° C.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with chloroform
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. customevaporated to dryness under reduced pressure
  5. washThe residue was deposited on a column of 250 g of silica gel and elution with a 7:3 chloroform-ethyl acetate mixture

Sources & evidence

ORD record
ord-d679c7f39af04c659478c42c33c8fb7f
Source dataset
uspto-grants-1986_05
Patent number
US04588720

Reaction notes

Loading…