Potassium Carbonate → HCID 57988782, compound

HRID 889058Notes

Reaction equation

HRID 889058 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:15]3[C:14](=[O:25])[N:13]([CH2:26][CH2:27][CH3:28])[C:12](=[O:29])[N:11]([CH2:30][CH2:31][CH3:32])[C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[CH3:33][O:34][C:35]([C:37]1(C)[CH2:41][CH:40](S(C)(=O)=O)[CH2:39][N:38]1[C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])=[O:36].[C:54]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:33][O:34][C:35]([CH:37]1[CH2:41][CH:40]([CH2:54][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:16]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:23])([CH3:22])[CH3:24])[C:15]4[C:14](=[O:25])[N:13]([CH2:26][CH2:27][CH3:28])[C:12](=[O:29])[N:11]([CH2:30][CH2:31][CH3:32])[C:10]=4[N:9]=3)=[CH:6][CH:7]=2)[CH2:39][N:38]1[C:46]([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:47])=[O:36]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86636560HCID 86636560, compoundHCID 135617740HCID 135617740, compound

Product 1

HCID 57988782HCID 57988782, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 8-(4-hydroxy-phenyl)-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6 dione (100 mg, 0.231 mmol), 4-methanesulfonyl methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (82 mg, 0.254 mmol) and K2CO3 (63 mg, 0.462 mmol) in DMF (8 ml) was heated at 80° C. for 3 hrs. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was washed with water, brine, dried over sodium sulphate, filtered and concentrated under vacuum. The residue obtained was purified by column chromatography to offer 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 as a yellow oil (110 mg, 36%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with ethyl acetate
  3. washThe filtrate was washed with water, brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-954d46bd9d374669b2cd8cf75e610897
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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