N-methoxy-N,2-dimethyl-3-nitrobenzamide → (4-Chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(2-methyl-3-nitro-phenyl)-methanone

HRID 916781Notes

Reaction equation

HRID 916781 reaction equation
C([Li])CCC.Br[C:7]1[C:15]2[C:14]([Cl:16])=[N:13][CH:12]=[N:11][C:10]=2[N:9]([CH:17]([CH3:19])[CH3:18])[CH:8]=1.CON(C)[C:23](=[O:34])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[C:25]=1[CH3:33]>C(OCC)C>[Cl:16][C:14]1[C:15]2[C:7]([C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[C:25]=3[CH3:33])=[O:34])=[CH:8][N:9]([CH:17]([CH3:19])[CH3:18])[C:10]=2[N:11]=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 15338107N-methoxy-N,2-dimethyl-3-nitrobenzamideHCID 457894285-Bromo-4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidineHCID 178418339Butyllithium

Product 1

HCID 86760551(4-Chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(2-methyl-3-nitro-phenyl)-methanoneYield 38%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

n-Butyllithium (2.5 M in hexanes, 14.3 mmol) was added dropwise to a suspension of 5-Bromo-4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine (3.7 g, 13.6 mmol) and ethyl ether (75 mL), cooled to −78 C, and stirred for 1 h. N-Methoxy-2,N-dimethyl-3-nitro-benzamide (4.0 g, 17.7 mmol) was added to the reaction mixture, stirred for 2 h, quenched with aqueous NH4Cl (100 mL), and extracted with EtOAc (3×100 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash column chromatography (silica, 3:7 EtOAc:hexanes) provided the title compound as an yellow solid (1.84 g, 38%). MS: 357.5 (MH−); HPLC Rf: 2.0 min. (HPLC method 2); HPLC purity: 100%.

Workup

  1. temperaturecooled to −78 C
  2. stirringstirred for 2 h
  3. customquenched with aqueous NH4Cl (100 mL)
  4. extractionextracted with EtOAc (3×100 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash column chromatography (silica, 3:7 EtOAc:hexanes)

Sources & evidence

ORD record
ord-cd2874cb1142436181110d2bfff8c204
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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