Potassium Hydroxide → HCID 86643045, compound

HRID 2192205Notes

Reaction equation

HRID 2192205 reaction equation
[OH-].[K+].[CH3:3][C@H:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([CH3:13])=[CH:9][CH:10]=2)[C@@H:5]1[NH:14][C:15]1[N:20]=[C:19]([NH2:21])[C:18]([C:22]#[C:23][Si](C)(C)C)=[CH:17][N:16]=1>CO.O>[CH3:3][C@H:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([CH3:13])=[CH:9][CH:10]=2)[C@@H:5]1[NH:14][C:15]1[N:20]=[C:19]([NH2:21])[C:18]([C:22]#[CH:23])=[CH:17][N:16]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67458051HCID 67458051, compound

Product 1

HCID 86643045HCID 86643045, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

0.427 g of potassium hydroxide is added to a mixture of 0.47 g (1.34 mmol) of N2-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-5-[(trimethylsilyl)ethynyl]pyrimidine-2,4-diamine (Ex.: 1.98) in 3 ml of methanol and 1 ml of water, the mixture is stirred for one hour at 25° C., concentrated by evaporation and taken up in water. Then, extraction is carried out with ethyl acetate, and the organic phase is dried and concentrated by evaporation. Following purification of the crude mixture by column-chromatographic separation, 0.139 g of N2-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-5-ethynylpyrimidine-2,4-diamine is obtained (yield 33% at 90% purity).

Workup

  1. concentrationconcentrated by evaporation
  2. extractionThen, extraction
  3. customthe organic phase is dried
  4. concentrationconcentrated by evaporation
  5. custompurification of the crude mixture
  6. customby column-chromatographic separation

Sources & evidence

ORD record
ord-88d5a768b20144fe9c8e53b60c6902ce
Source dataset
uspto-grants-2012_12
Patent number
US08329717B2

Reaction notes

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