Hydrochloric Acid → 4-{4-[2-Amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-phenyl}-butyric acid

HRID 28613Notes

Reaction equation

HRID 28613 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=3[O:28][CH2:29][CH3:30])[N:18]=[C:17]([NH2:31])[N:16]=2)=[CH:10][CH:9]=1)C.[OH-].[Na+].[Cl-].[Na+].Cl>C(OCC)(=O)C.C(O)C>[NH2:31][C:17]1[N:16]=[C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][CH2:5][C:4]([OH:32])=[O:3])=[CH:9][CH:10]=2)[CH:20]=[C:19]([C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=2[O:28][CH2:29][CH3:30])[N:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 68984977HCID 68984977, compound

Product 1

HCID 114871474-{4-[2-Amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-phenyl}-butyric acidYield 66%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-{4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-phenyl}-butyric acid ethyl ester (350 mg, 0.71 mmol), sodium hydroxide (150 mg, 3.8 mmol) and ethanol (5 ml) was stirred for 18 hours. Ethyl acetate (100 ml), saturated aqueous sodium chloride solution (100 ml) and concentrated hydrochloric acid (1 ml) were added and the mixture was stirred for 10 minutes. The organic layer was concentrated under reduced pressure. The residual solid was treated with water (25 ml) and stirred vigorously. Suction filtration afforded the title compound (200 mg 61% yield) as a white powder. 1H NMR (DMSO-d6) δ 1.38 (m, 3H, CH3), 1.83 (m, 2H, CH2), 2.23 (m, 2H, CH2), 2.61 (m, 2H, CH2), 4.17 (m, 2H, CH2), 6.60 (s, 1H, Ar), 7.20-7.29 (m, 3H, Ar), 7.61-7.71 (m, 4H, Ar), 10.76 (s, 1H, NH), 12.48 (s, 1H).

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. additionThe residual solid was treated with water (25 ml)
  4. stirringstirred vigorously
  5. filtrationSuction filtration

Sources & evidence

ORD record
ord-741cf50928e7484ab5904c68f551e9be
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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