Chloroiodomethane → HCID 178486720, compound

HRID 896061Notes

Reaction equation

HRID 896061 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[N:8][CH:7]=[C:6]2[CH2:15][C:16]1[NH:24][C:23]2[C:22](=[O:25])[N:21]([CH3:26])[C:20](=[O:27])[N:19]([CH2:28][C:29]([CH3:31])=[CH2:30])[C:18]=2[N:17]=1.[CH2:32]([Zn]CC)C.ClCI>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[N:8][CH:7]=[C:6]2[CH2:15][C:16]1[NH:17][C:18]2[N:19]([CH2:28][C:29]3([CH3:32])[CH2:31][CH2:30]3)[C:20](=[O:27])[N:21]([CH3:26])[C:22](=[O:25])[C:23]=2[N:24]=1

Participants

5

Reactant 3

HCID 11644ChloroiodomethaneHCID 22226562HCID 22226562, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 178486720HCID 178486720, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The product of Example 18, 8-(6,7-dimethoxy-isoquinolin-4-ylmethyl)-1-methyl-3-(2-methyl-allyl)-3,7-dihydro-purine-2,6-dione (100 mg, 0.24 mmol) is suspended in 1,2-dichloroethane (30 ml). Diethyl zinc (1M hexane solution, 1.2 ml, 1.20 mmol) is added, followed by chloroiodomethane (0.174 ml, 0.24 mmol) and the reaction is stirred at ambient temperature for 1 hour, prior to quenching with saturated aqueous NH4Cl. After extraction with chloroform, the organic phase is washed with water, dried over MgSO4 and evaporated. Purification by preparative HPLC affords 8-(6,7-dimethoxyisoquinolin-4-ylmethyl)-1-methyl-3-(l -methyl-cyclopropylmethyl)-3,9-dihydro-purine-2,6-dione, [MH]+ 436.

Workup

  1. customto quenching with saturated aqueous NH4Cl
  2. extractionAfter extraction with chloroform
  3. washthe organic phase is washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-d86c5ff0224740ecb17df81d49cffe66
Source dataset
uspto-grants-2005_07
Patent number
US06919337B2

Reaction notes

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