Hydrochloric Acid → HCID 21833455, compound

HRID 1740859Notes

Reaction equation

HRID 1740859 reaction equation
C([O:3][C:4]([C:6]1[C:7]([NH:18][CH2:19][C:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])=[O:21])=[N:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=O)C.[BH4-].[Na+].[Cl-].[Li+].Cl>C(O)C.O1CCCC1>[OH:3][CH2:4][C:6]1[C:7]([NH:18][CH2:19][C:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])=[O:21])=[N:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 21833451HCID 21833451, compound

Product 1

HCID 21833455HCID 21833455, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(5-ethoxycarbonyl-2-phenyl-4-pyrimidinylamino)-N,N-dipropylacetamide (3.0 g) obtained in Example 126, sodium borohydride (0.6 g), lithium chloride (0.7 g) and tetrahydrofuran (20 ml) is added dropwise anhydrous ethanol (30 ml) at 0 to 5° C. The reaction mixture is stirred at room temperature for five hours, and the pH value thereof is adjusted to pH 5 with 1N hydrochloric acid, and concentrated under reduced pressure. To the residue are added a brine and chloroform, and the chloroform layer is collected, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from isopropanol to give the desired compound (2.0 g), m.p. 167-168° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue are added a brine and chloroform
  3. customthe chloroform layer is collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent; chloroform)
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-1e0fb48488b346b0a0df1d40b6bf7501
Source dataset
uspto-grants-1999_10
Patent number
US05972946

Reaction notes

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