HCID 57988782, compound → 4-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-pyrrolidine-2-carboxylic acid methyl ester

HRID 889059Notes

Reaction equation

HRID 889059 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:26](COCC[Si](C)(C)C)[C:25]4[C:24](=[O:35])[N:23]([CH2:36][CH2:37][CH3:38])[C:22](=[O:39])[N:21]([CH2:40][CH2:41][CH3:42])[C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:7][N:6]1C(OC(C)(C)C)=O)=[O:4]>CO.Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[NH:26][C:25]4[C:24](=[O:35])[N:23]([CH2:36][CH2:37][CH3:38])[C:22](=[O:39])[N:21]([CH2:40][CH2:41][CH3:42])[C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:7][NH:6]1)=[O:4]

Participants

4

Reactant 1

HCID 57988782HCID 57988782, compound

Product 1

HCID 579887884-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-pyrrolidine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 4-{4-[2,6-Dioxo-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]-phenoxymethyl}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (100 mg) in methanol (3 ml), methanolic HCl (3 N, 0.5 ml) was added at 0° C., reaction mixture was stirred at room temperature for 2 hrs. The reaction mixture was evaporated and the residue obtained was purified by column chromatography to offer 4-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-pyrrolidine-2-carboxylic acid methyl ester as a yellow solid (50 mg, 74%).

Workup

  1. customreaction mixture
  2. customThe reaction mixture was evaporated
  3. customthe residue obtained
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-7356eff818854849aa85ce74b055624c
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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