Isopropanol → 4-tert-butyl-N-[6-{2-(5-(1-hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide

HRID 2275Notes

Reaction equation

HRID 2275 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]([O:10][CH2:11][CH2:12][O:13][C:14]2[N:19]=[CH:18][N:17]=[C:16]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:15]=2[O:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH3:42])[CH:36]=2)=[N:8][CH:9]=1)(=[O:3])[CH3:2].O1CCCC1.C(O)(C)C.[BH4-].[Na+]>O>[C:30]([C:27]1[CH:26]=[CH:25][C:24]([S:21]([NH:20][C:16]2[C:15]([O:34][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH3:42])[CH:36]=3)=[C:14]([O:13][CH2:12][CH2:11][O:10][C:7]3[N:8]=[CH:9][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][N:6]=3)[N:19]=[CH:18][N:17]=2)(=[O:23])=[O:22])=[CH:29][CH:28]=1)([CH3:33])([CH3:31])[CH3:32]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydride2×HCID 19689514HCID 19689514, compound

Product 1

HCID 196894724-tert-butyl-N-[6-{2-(5-(1-hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamideYield 75.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of N-[6-{2-(5-acetylpyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (756 mg), tetrahydrofuran (10 ml) and isopropyl alcohol (10 ml) is added with stirring sodium borohydride (48 mg) under ice-cooling, and the mixture is stirred for 40 minutes under ice-cooling. To the reaction solution is further added sodium borohydride (14 mg), and the mixture is stirred for 30 minutes. The mixture is diluted with water, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and concentrated to dryness under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1~20:1), and recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-[6-{2-(5-(1-hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide (571 mg) as crystals.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture is stirred for 30 minutes
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer is washed
  6. customdried
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1~20:1)
  9. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-d12ed1b9d8ff40f987297e00a881f389
Source dataset
uspto-grants-1998_03
Patent number
US05728706

Reaction notes

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