Tetrahydrofuran → HCID 68705075, compound

HRID 1744969Notes

Reaction equation

HRID 1744969 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[CH2:10][CH2:11][CH2:12][C:8]=2[N:7]=[C:6]([NH2:13])[N:5]=1)C.Br[CH2:15][C:16](=O)[C:17]([O-:19])=[O:18].[CH2:21]1COC[CH2:22]1>>[CH2:21]([O:19][C:17]([C:16]1[N:13]=[C:6]2[N:7]([C:8]3[CH2:12][CH2:11][CH2:10][C:9]=3[C:4]([O:3][CH3:1])=[N:5]2)[CH:15]=1)=[O:18])[CH3:22]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 6994776Propanoic acid, 3-bromo-2-oxo-, ion(1-)HCID 12290586HCID 12290586, compound

Product 1

HCID 68705075HCID 68705075, compound

Conditions

Temperature
23 °C

Procedure

4.8 gram (29 mmol) 4-ethoxy-6,7-dihydro-5H-cyclopentapyrimidin-2-ylamine was dissolved in 100 ml dry THF. Bromopyruvate (5.4 ml,) was then added dropwise with in five minutes. The mixture was stirred at 23° C. for one hour. It was then filtered and washed with ether to give 8.7 gram of solid. This solid was then dissolved in 50 ml ethanol and refluxed for two hours. The reaction mixture was cooled to room temperature and partitioned between 350 ml chloroform and 200 ml saturated sodium bicarbonate. The organic layer was separated and dried over magnesium sulfate. Filter off the drying agent and concentrate to give 5.3 gram of product (70% Yield). MP: 105–106° C. (M+H) 262.

Workup

  1. filtrationIt was then filtered
  2. washwashed with ether

Sources & evidence

ORD record
ord-9b45b119ae694b95bb3114affae44ff8
Source dataset
uspto-grants-2006_03
Patent number
US07018997B2

Reaction notes

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