HCID 178418546, compound → HCID 178437725, compound

HRID 1458645Notes

Reaction equation

HRID 1458645 reaction equation
[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[C:17](I)=[C:16]([CH2:19][CH3:20])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Cu][C:22]#[N:23]>O.ClCCl>[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[C:17]([C:22]#[N:23])=[C:16]([CH2:19][CH3:20])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 178418546HCID 178418546, compoundHCID 178437728HCID 178437728, compound

Product 1

HCID 178437725HCID 178437725, compound

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

1.8 g (5 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-6-ethyl-5-iodopyrimidine (Example 1) and 1.0 g of copper(I) cyanide were stirred at 200° C. for 30 minutes without solvent. After cooling, the mixture was taken up in water/dichloromethane, the organic phase was again extracted by stirring with aqueous ammonia solution, and the extract was dried and concentrated. The crude product was purified by chromatography on silica gel using petroleum ether/ethyl acetate (7:3), to give 750 mg (52.4% of theory) of a colorless oil which crystallized on standing.

Workup

  1. temperatureAfter cooling
  2. extractionthe organic phase was again extracted
  3. customthe extract was dried
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography on silica gel
  6. customto give 750 mg (52.4% of theory) of a colorless oil which
  7. customcrystallized

Sources & evidence

ORD record
ord-8314f2921f65498289cf68f4ff576cf3
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

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