Tetrahydrofuran → HCID 59380164, compound

HRID 2353685Notes

Reaction equation

HRID 2353685 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[C:18]([C:20]([O:22]C)=[O:21])[CH:17]=[C:16]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]4[CH3:30])[N:15]=3)=[CH:10][CH:9]=2)=[O:6])[CH2:3][CH2:2]1.[OH-].[Na+].C1COCC1>O>[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[C:18]([C:20]([OH:22])=[O:21])[CH:17]=[C:16]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]4[CH3:30])[N:15]=3)=[CH:10][CH:9]=2)=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2×HCID 59380000HCID 59380000, compound

Product 1

HCID 59380164HCID 59380164, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2-[4-(cyclopropylcarbamoylamino)phenyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine-4-carboxylate (350 mg) was dissolved in water (15 mL) containing sodium hydroxide (67 mg) and the reaction was allowed to stir at RT for 1 h. A further 2 equivalents of sodium hydroxide were added along with THF (3 mL). The reaction was stirred for another 1 h then the THF removed under reduced pressure and the aqueous solution partitioned with ethyl acetate (15 mL). The aqueous layer was acidified with concentrated hydrochloric acid and the precipitate was filtered and dried in a vac-oven at 50° C. for 18 h to give the desired material (350 mg) as a white solid.

Workup

  1. stirringThe reaction was stirred for another 1 h
  2. customthe THF removed under reduced pressure
  3. customthe aqueous solution partitioned with ethyl acetate (15 mL)
  4. filtrationthe precipitate was filtered
  5. customdried in a vac-oven at 50° C. for 18 h

Sources & evidence

ORD record
ord-d3d16ae322534f46849dc0fb97e4cca9
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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