Hydrochloric Acid → {[1-({[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)cyclobutyl]methoxy}-acetic acid

HRID 2189127Notes

Reaction equation

HRID 2189127 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][O:8][CH2:9][C:10]1([CH2:14][O:15][C:16]2[C:17]3[C:24]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)=[C:23]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[O:22][C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:13][CH2:12][CH2:11]1)(C)(C)C.Cl>O1CCOCC1>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]2[C:17]3[C:16]([O:15][CH2:14][C:10]4([CH2:9][O:8][CH2:7][C:6]([OH:39])=[O:5])[CH2:11][CH2:12][CH2:13]4)=[N:21][CH:20]=[N:19][C:18]=3[O:22][C:23]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58280083{[1-({[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)cyclobutyl]methoxy}-acetic acid tert-butyl ester

Product 1

HCID 58280202{[1-({[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)cyclobutyl]methoxy}-acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Dissolve 237 mg (0.45 mmol) of {[1-({[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)cyclobutyl]methoxy}acetic acid tert-butyl ester in 1 ml of dioxane, add 2 ml of 4 N hydrogen chloride in dioxane and stir at RT for 16 h. After concentrating the reaction solution under reduced pressure, purify the residue by means of preparative RP-HPLC (gradient: water/acetonitrile). 180 mg (85% of theory) of the desired product are obtained.

Workup

  1. concentrationAfter concentrating the reaction solution under reduced pressure
  2. custompurify the residue by means of preparative RP-HPLC (gradient: water/acetonitrile)

Sources & evidence

ORD record
ord-8ffe6d8372404493b73e67696bddef75
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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