5-Bromo-4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine → HCID 86603158, compound

HRID 736354Notes

Reaction equation

HRID 736354 reaction equation
[Li]CCCC.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.[C:20](=[N:33][C:34]1[CH:35]=[C:36]([CH:43]=[C:44]([O:46][CH3:47])[N:45]=1)[C:37](N(OC)C)=[O:38])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCOCC>[C:20](=[N:33][C:34]1[CH:35]=[C:36]([C:37]([C:7]2[C:15]3[C:14]([Cl:16])=[N:13][CH:12]=[N:11][C:10]=3[N:9]([CH:17]([CH3:19])[CH3:18])[CH:8]=2)=[O:38])[CH:43]=[C:44]([O:46][CH3:47])[N:45]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 457894285-Bromo-4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidineHCID 86603157HCID 86603157, compoundHCID 178418339Butyllithium

Product 1

HCID 86603158HCID 86603158, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

n-BuLi (9.40 mL, 2.5 M in Hexane, 23.3 mmol) was added dropwise to a solution of 5-Bromo-4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine (6.25 g, 22.2 mmol) in Et2O (190 mL) at −78° C. and stirred for 1 h. 2-(Benzhydrylidene-amino)-6,N-dimethoxy-N-methyl-isonicotinamide (10.0 g, 26.6 mmol) was added to the reaction mixture slowly and stirred for 3h, warmed to room temperature, and quenched with saturated aqueous NH4Cl (200 mL). The aqueous layer was extracted with EtOAc (3×200 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to provide a crude solid. Purification by flash column chromatography (ethyl acetate/hexanes 1:1) afforded the title compound as a yellow solid (7.31 mg, 63%). MS: 511.3 (MH+); HPLC Rf: 3.1 min. (HPLC method 3); HPLC purity: 100%.

Workup

  1. customquenched with saturated aqueous NH4Cl (200 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (3×200 mL)
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a crude solid
  7. customPurification by flash column chromatography (ethyl acetate/hexanes 1:1)

Sources & evidence

ORD record
ord-4211d2d31e9a4640818b843d2d3ce26b
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

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