HCID 58015954, compound → HCID 58015783, compound

HRID 2189289Notes

Reaction equation

HRID 2189289 reaction equation
Br[C:2]1(Br)[C:10]2[CH:9]=[N:8][C:7]([Cl:11])=[N:6][C:5]=2[N:4]([CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[C:3]1=[O:17]>C(O)(=O)C.C1COCC1.[Zn]>[Cl:11][C:7]1[N:8]=[CH:9][C:10]2[CH2:2][C:3](=[O:17])[N:4]([CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[C:5]=2[N:6]=1

Participants

5

Reactant 1

HCID 58015954HCID 58015954, compound

Product 1

HCID 58015783HCID 58015783, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5,5-dibromo-2-chloro-7-(1-ethyl-propyl)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (crude, ˜5.3 mmol) in acetic acid (6 mL) and THF (4 mL) is added Zn dust (1.37 g, 21 mmol) at 0° C. The mixture is stirred at 0° C. for 2 min then warmed up to room temperature, stirred for 30 min. The mixture is filtered through a pad of Celite, rinsed with ethyl acetate. The filtrate is concentrated in vacuo and the residue is purified by flash chromatography (SiO2, EtOAc/hexane 5:95 to 40:60) to give 2-chloro-7-(1-ethyl-propyl)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one.

Workup

  1. temperaturethen warmed up to room temperature
  2. stirringstirred for 30 min
  3. filtrationThe mixture is filtered through a pad of Celite
  4. washrinsed with ethyl acetate
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe residue is purified by flash chromatography (SiO2, EtOAc/hexane 5:95 to 40:60)

Sources & evidence

ORD record
ord-97e61d2cbe5d4d37a7a754158f9abb71
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

Loading…