5-Iodo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine → (5-Bromo-6-ethoxy-pyridin-3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

HRID 82268Notes

Reaction equation

HRID 82268 reaction equation
I[C:2]1[C:10]2[CH:9]=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH:11]([CH3:13])[CH3:12])[CH:3]=1.[Li]CCCC.[Br:19][C:20]1[C:21]([O:32][CH2:33][CH3:34])=[N:22][CH:23]=[C:24]([CH:31]=1)[C:25](N(OC)C)=[O:26]>C(OCC)C.CCCCCC>[Br:19][C:20]1[CH:31]=[C:24]([C:25]([C:2]2[C:10]3[CH:9]=[N:8][CH:7]=[N:6][C:5]=3[N:4]([CH:11]([CH3:13])[CH3:12])[CH:3]=2)=[O:26])[CH:23]=[N:22][C:21]=1[O:32][CH2:33][CH3:34]

Participants

6

Reactant 3

HCID 708171765-Iodo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidineHCID 86672122HCID 86672122, compoundHCID 178418339Butyllithium2×

Product 1

HCID 70817466(5-Bromo-6-ethoxy-pyridin-3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanoneYield 49%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 5-Iodo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine (Preparation 93, 530 mg, 1.85 mmol) in anhydrous diethyl ether (8 mL) was cooled to −78° C. under nitrogen and n-BuLi (1 mL of a 2.03M solution in Hexane, 2.03 mmol) was added drop wise over a period of 10 min. Just after the completion of addition of n-BuLi, a solution of 5-Bromo-6-ethoxy-N-methoxy-N-methyl-nicotinamide (Preparation 240) in anhydrous diethyl ether (7 mL) was added slowly to the mixture and it was stirred at the same temperature for another 1 hour. The reaction mixture was warmed to room temperature and allowed to stir for another hour before being quenched with sat. aq. NH4Cl (15 mL). The mixture was extracted with EtOAc (3×15 mL), washed with water (20 mL), brine (15 mL), dried (Na2SO4) and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (EtOAc:petroleum ether 2:10) to afford the title compound as a yellow gum in 49% yield, 350 mg.

Workup

  1. stirringto stir for another hour
  2. custombefore being quenched with sat. aq. NH4Cl (15 mL)
  3. extractionThe mixture was extracted with EtOAc (3×15 mL)
  4. washwashed with water (20 mL), brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe crude material was purified by column chromatography on silica gel (EtOAc:petroleum ether 2:10)

Sources & evidence

ORD record
ord-5de769f660b34edc9a80996145400139
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

Loading…