Dimethylformamide → Methyl 3-((6-amino-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzoate

HRID 2197448Notes

Reaction equation

HRID 2197448 reaction equation
[NH2:1][C:2]1[N:10]=[C:9](Cl)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17].[C:23](=[O:26])([O-])[O-].[K+].[K+].I[CH3:30].CN(C)[CH:33]=[O:34]>>[NH2:1][C:2]1[N:10]=[C:9]([O:34][CH2:33][CH2:30][O:26][CH3:23])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57816807Methyl 3-((6-amino-2-chloro-9H-purin-9-yl)methyl)benzoate

Product 1

HCID 57816768Methyl 3-((6-amino-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzoateYield 65%

Procedure

A solution of Compound (3) (13.69 g) and potassium carbonate (8.75 g, 63.28 mmol) in DMF (“dimethylformamide”) (20 mL) was cooled to 0° C. Iodomethane (6.74 g, 47.46 mmol) was added to the solution and the mixture was allowed to warm to room temperature. After 30 minutes, the reaction was complete and was quenched with acetic acid. The quenched reaction mixture was extracted with ethyl acetate to give Compound (4) (7.36 g, 65% over two steps). 1H NMR (300 MHz, CDCl3) δ 3.43 (s, 3H), 3.77 (t, J=5.4, 10.2 Hz, 2H), 3.92 (s, 3H), 4.51 (t, J=4.8, 9.9 Hz, 2H), 5.32 (s, 2H), 7.45 (m, 3H), 7.65 (s, 1H), 8.03 (s, 1H). LCMS: m/z for C17H19N5O4++H observed 358.1 at 3.62 minutes of a 6 minute run, gradient 5-95% CH3CN in H2O. LCMS: m/z for C17H19N5O4++H observed 358.1 at 1.93 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O (C18 column).

Workup

  1. customwas quenched with acetic acid
  2. customThe quenched reaction mixture
  3. extractionwas extracted with ethyl acetate

Sources & evidence

ORD record
ord-a3e29622b4284835840207f51fda78d3
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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