Water → HCID 178473678, compound

HRID 1241346Notes

Reaction equation

HRID 1241346 reaction equation
[CH2:1]([O:3][P:4]([C:9]([O:32][CH2:33][CH3:34])([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:27]=[C:26](I)[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[CH:29]([CH3:31])[CH3:30])=[CH:14][CH:13]=1)[PH2:10]=[O:11])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[Br-].[CH:36]1([Zn+])[CH2:40][CH2:39][CH2:38][CH2:37]1.O>CN(C=O)C>[CH2:1]([O:3][P:4]([C:9]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:27]=[C:26]([CH:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[CH:29]([CH3:31])[CH3:30])=[CH:14][CH:13]=1)([O:32][CH2:33][CH3:34])[PH2:10]=[O:11])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 178419768HCID 178419768, compoundHCID 178473679HCID 178473679, compound

Product 1

HCID 178473678HCID 178473678, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To {ethoxy-[4-(2-iodo-9-isopropyl-9H-purin-6-ylamino)-phenyl]-phosphinoylmethyl}-phosphonic acid diethyl ester (0.30 g, 0.48 mmol) in DMF (3.9 mL) was added PdCl2(PPh3)4 (17 mg, 0.024 mmol) followed by cyclopentylzinc bromide (0.5M THF, 3.9 mL, 1.9 mmol). The mixture was stirred at rt for 1 h, poured into water and extracted with EtOAc. The combined extracts, were washed with water, sat'd NaCl, then dried over MgSO4 and filtered. The material was used without purification in the next reaction.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts, were washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe material was used without purification in the next reaction

Sources & evidence

ORD record
ord-cdbe193546264b9dbfec3b871031f774
Source dataset
uspto-grants-2006_10
Patent number
US07115589B2

Reaction notes

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