Methyl iodide → HCID 21883031, compound

HRID 722100Notes

Reaction equation

HRID 722100 reaction equation
[Br:1][C:2]1[C:22]([O:23][CH3:24])=[C:21]([O:25][CH3:26])[C:20]([O:27][CH3:28])=[CH:19][C:3]=1[CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][C:8]([NH:15][C:16](=[O:18])[CH3:17])=[N:9][C:10]=2[Cl:14].[H-].[Na+].[CH3:31]I>CN(C=O)C>[Br:1][C:2]1[C:22]([O:23][CH3:24])=[C:21]([O:25][CH3:26])[C:20]([O:27][CH3:28])=[CH:19][C:3]=1[CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][C:8]([N:15]([CH3:31])[C:16](=[O:18])[CH3:17])=[N:9][C:10]=2[Cl:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21882936HCID 21882936, compound

Product 1

HCID 21883031HCID 21883031, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[9-(2-bromo-3,4,5-trimethoxy-benzyl)-6-chloro-9H-purin-2-yl]-acetamide and NaH in DMF was stirred at r.t. for 15 min, before adding MeI. Stirring was prolonged for 2 h at 50° C. Work-up and purification by preparative TLC (EtOAc:hexane 1:1) gave the title compound. HPLC Rt: 6.422 min. 1H-NMR (CDCl3): δ 8.20 (s, 1H), 6.80 (s, 1H), 5.45 (s, 2H), 3.93 (s, 3H), 3.90 (s, 3H), 3.82 (s, 3H), 3.57 (s, 3H), 2.51 (s, 3H).

Workup

  1. stirringStirring
  2. waitwas prolonged for 2 h at 50° C
  3. custompurification by preparative TLC (EtOAc:hexane 1:1)

Sources & evidence

ORD record
ord-9af70aeca09648a39b660f60e78bc943
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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