Hydrochloric Acid → HCID 49788293, compound

HRID 1400189Notes

Reaction equation

HRID 1400189 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)[O:8][C:7]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:5])C.[H][H].CCO.[OH-].[Na+].Cl>>[NH2:17][C:13]1[N:12]=[C:11]([C:9]2[O:8][C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=2)[CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 49787899HCID 49787899, compoundHCID 178473701HCID 178473701, compound

Product 1

HCID 49788293HCID 49788293, compound

Conditions

Temperature
100 °C

Procedure

To a solution of ester 59 (221 mg, 0.71 mmol) in 1:1 H2/EtOH (9 mL), 4M aq NaOH (10 eq) was added and the reaction mixture was stirred at 100° C. for 1 h. After cooling to rt, the solution was acidified with 2M HCl yielding 5-(2-amino-pyrimidin-4-yl)-2-phenyl-furan-3-carboxylic acid as a white solid which was filtered, washed with water and dried under reduced pressure (quant.).

Workup

  1. temperatureAfter cooling to rt

Sources & evidence

ORD record
ord-8e5329160aeb4b3ea356c44aa636d544
Source dataset
uspto-grants-2014_12
Patent number
US08906934B2

Reaction notes

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