Benzoyl chloride, 3,4,5-trimethoxy- → (2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3,4,5-trimethoxy-phenyl)-methanone

HRID 273348Notes

Reaction equation

HRID 273348 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[CH:11]=[CH:10][NH:9][C:7]=2[N:8]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[C:17](Cl)=[O:18].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.C([Mg]Br)C.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[C:11]([C:17]([C:16]3[CH:20]=[C:21]([O:25][CH3:26])[C:22]([O:23][CH3:24])=[C:14]([O:13][CH3:12])[CH:15]=3)=[O:18])=[CH:10][NH:9][C:7]=2[N:8]=1

Participants

7

Reactant 3

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 6451240Aluminum(III) ChlorideHCID 101033172-Methoxy-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 52951494(2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3,4,5-trimethoxy-phenyl)-methanoneYield 20%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent2×HCID 178418443HCID 178418443, compoundSolvent

Procedure

To a mixture of 2-methoxy-7H-pyrrolo[2,3-d]pyrimidine (0.220 g, 1.476 mmol) and anhydrous zinc chloride (0.407 g, 2.953 mmol) in dry CH2Cl2 (20 mL), ethylmagnesium bromide (0.65 mL, 3.0 M solution in diethyl ether) was added over 10 min at room temperature. The suspension was stirred for 1 h, and then 3,4,5-trimethoxybenzoyl chloride (0.510 g, 2.2 mmol) in dry CH2Cl2 (10 mL) was added dropwise over 5 min. The reaction mixture was stirred for another 1 h and then aluminum chloride (0.196 mg, 1.476 mmol) was added. The resulting thick mixture was vigorously stirred for 5 h. The reaction was quenched with water (10 mL) and extracted with CH2Cl2 (20 mL). The combined organic layers were dried over anhydrous MgSO4 and evaporated to give a brown oil, which was purified on a silica gel column (EtOAc:Hexane=1:1 to MeOH:CH2Cl2=1:20) to give compound 16 (0.081 g, 20%).

Workup

  1. additionwas added over 10 min at room temperature
  2. stirringThe reaction mixture was stirred for another 1 h
  3. stirringThe resulting thick mixture was vigorously stirred for 5 h
  4. customThe reaction was quenched with water (10 mL)
  5. extractionextracted with CH2Cl2 (20 mL)
  6. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  7. customevaporated
  8. customto give a brown oil, which
  9. customwas purified on a silica gel column (EtOAc:Hexane=1:1 to MeOH:CH2Cl2=1:20)

Sources & evidence

ORD record
ord-003970a2dac0427da840d98cc4c63d9f
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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