HCID 58015954, compound → HCID 58015783, compound

HRID 2189262Notes

Reaction equation

HRID 2189262 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 mins then heated to room temperature, stirring for 30 mins. The mixture is filtered through celite, rinsed with ethyl acetate. The filtrate is concentrated in vacuo and the residue is purified by flash chromatography (ethyl acetate: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 heated to room temperature
  2. stirringstirring for 30 mins
  3. filtrationThe mixture is filtered through celite
  4. washrinsed with ethyl acetate
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe residue is purified by flash chromatography (ethyl acetate:hexane=5:95 to 40:60)

Sources & evidence

ORD record
ord-87208ebeb0a1429dafcda18ecfad2601
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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