Sodium Hydroxide → HCID 25095644, compound

HRID 2189108Notes

Reaction equation

HRID 2189108 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:15]3[C:22]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)=[C:21]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[O:20][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:9][CH:8]=1.[OH-].[Na+]>C1COCC1>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]2[C:15]3[C:14]([NH:13][C:10]4[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][CH2:4][C:3]([OH:37])=[O:2])=[CH:8][CH:9]=4)=[N:19][CH:18]=[N:17][C:16]=3[O:20][C:21]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 25095643HCID 25095643, compound

Product 1

HCID 25095644HCID 25095644, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 175.6 mg (0.356 mmol) of 4-(4-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenyl)butanoic acid methyl ester in 3.5 ml of THF, add 1.07 ml of 1N sodium hydroxide solution at RT and stir at 50° C. for 1 h. Cool to RT and remove the THF under reduced pressure. Add water to the residue, and then 1N hydrochloric acid. Filter off the precipitated solid, wash repeatedly with water and dry at 40° C. under reduced pressure overnight. 130 mg (76.2% of theory) of the target compound are obtained as a white solid.

Workup

  1. temperatureCool to RT
  2. customremove the THF under reduced pressure
  3. filtrationFilter off the precipitated solid
  4. washwash repeatedly with water
  5. customdry at 40° C. under reduced pressure overnight
  6. custom130 mg (76.2% of theory) of the target compound are obtained as a white solid

Sources & evidence

ORD record
ord-8dc08467836a467a9cc76f7b858b1b60
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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