Dimethylformamide → HCID 18706853, compound

HRID 1421875Notes

Reaction equation

HRID 1421875 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11]2)[CH:5]=[C:4]([Cl:16])[N:3]=1.[Cl:17]N1C(=O)CCC1=O.CN(C)C=O>C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11]2)[C:5]([Cl:17])=[C:4]([Cl:16])[N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 385223HCID 385223, compound

Product 1

HCID 18706853HCID 18706853, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 2-amino-6-chloro-4-[[(1-hydroxymethyl-1-cyclobutyl)methyl]amino]pyrimidine (0.24 g, 2.0 mmol) were added N-chlorosuccinimide (0.27 g, 2.0 mmol) and dimethylformamide (1.5 ml), and the mixture was stirred at room temperature for 2 days. Ethyl acetate was added and the mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to give colorless prism crystals (0.3 g, 54.2%), m.p. 179-181° C. (acetone).

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-225cb617e10e4cb4ba5b09eccd0edbd6
Source dataset
uspto-grants-2000_06
Patent number
US06080750

Reaction notes

Loading…