Water → HCID 178433185, compound

HRID 1458666Notes

Reaction equation

HRID 1458666 reaction equation
[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[C:17]([CH2:18][CH2:19]O)=[C:16]([CH3:21])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:28])CC)C.O>ClCCl>[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[C:17]([CH2:18][CH2:19][F:28])=[C:16]([CH3:21])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 178433186HCID 178433186, compound

Product 1

HCID 178433185HCID 178433185, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g (6.5 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-6-methyl-5-(2-hydroxyethyl)pyrimidine (Example 33) were dissolved in 30 ml of dichloromethane, and 1.16 g (7.2 mmol) of diethylaminosulfur trifluoride (DAST) were added at -50° C. The mixture was allowed to rise to room temperature, and was subsequently stirred for 4 hours. It was poured into water, the dichloromethane phase was extracted by stirring with sodium hydrogen carbonate solution and the organic extracts were dried and concentrated. Chromatography on silica gel gave 1.55 g (77.6% of theory) of product as colorless oil.

Workup

  1. customto rise to room temperature
  2. extractionthe dichloromethane phase was extracted
  3. stirringby stirring with sodium hydrogen carbonate solution
  4. customthe organic extracts were dried
  5. concentrationconcentrated
  6. customChromatography on silica gel gave 1.55 g (77.6% of theory) of product as colorless oil

Sources & evidence

ORD record
ord-1d31cfb9afd8472f917b9b99ea8632eb
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

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