Dimethyl Sulfoxide → HCID 80864926, compound

HRID 1504554Notes

Reaction equation

HRID 1504554 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.CC(C)([O-])C.[K+].[CH:15]1([CH2:18][OH:19])[CH2:17][CH2:16]1.CS(C)=O>O.CCOC(C)=O>[CH:15]1([CH2:18][O:19][C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=2)[CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 75644CyclopropanemethanolHCID 2380124-Amino-6-chloropyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 80864926HCID 80864926, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A vial was charged with 6-chloropyrimidin-4-amine (0.200 g, 1.544 mmol), potassium tert-butoxide (0.381 g, 3.40 mmol), cyclopropylmethanol (0.223 g, 3.09 mmol), and dimethyl sulfoxide (3.09 ml). The vial was capped and the reaction was heated to 100° C. After 3 hour, the mixture was diluted with water and EtOAc. The layers were separated, and the aq. layer was extracted with EtOAc (2×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (40 g Redi-Sep Gold column, 0-50% of EtOAc/heptane to give 6-(cyclopropylmethoxy)pyrimidin-4-amine (0.189 g, 1.144 mmol, 74.1% yield) as a white solid. In/z (ESI) 166.2 (M+H)+.

Workup

  1. customThe vial was capped
  2. customThe layers were separated
  3. extractionthe aq. layer was extracted with EtOAc (2×)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (40 g Redi-Sep Gold column, 0-50% of EtOAc/heptane

Sources & evidence

ORD record
ord-38dfabd43f164dc19df3a40d919e89ff
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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