Potassium Hydroxide → N-tert-butyl-4-ethynylpyrimidin-2-amine

HRID 885635Notes

Reaction equation

HRID 885635 reaction equation
[C:1]([NH:5][C:6]1[N:11]=[C:10]([C:12]#[C:13][Si](C)(C)C)[CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>CO>[C:1]([NH:5][C:6]1[N:11]=[C:10]([C:12]#[CH:13])[CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 121652332-tert-Butylamino-4-[trimethylsilylethynyl]pyrimidine

Product 1

HCID 12165235N-tert-butyl-4-ethynylpyrimidin-2-amineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of 2-tert-butylamino-4-[trimethylsilylethynyl]pyrimidine (from Example 2) in CH3OH (150 mL) was treated with a solution of KOH (30 mg) in CH3OH (5 mL). After 30 min, additional KOH (30 mg) in CH3OH (5 mL) was added. After a further 30 min, the mixture was concentrated and the residue was diluted with hexanes and loaded directly onto a short pad of SiO2. The product was eluted with 10% EtOAc in hexanes to provide the crude product as a light brown oil (18.6 g, 90% for 2 steps), which was used without further purification. TLC: Rf=0.29. IR: 3294 (m), 2965 (m), 2114 (w), 1571 (s). 1H NMR: 8.23 (d, J=5.0 Hz, 1H), 6.60 (d, J=5.0 Hz, 1H), 5.20 (s, 1H), 3.15 (s, 1H), 1.43 (s, 9H). 13C NMR: 161.97, 157.99, 149.87, 112.63, 81.71, 78.72, 51.06, 28.80.

Workup

  1. waitAfter a further 30 min
  2. concentrationthe mixture was concentrated
  3. additionthe residue was diluted with hexanes
  4. washThe product was eluted with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-c7606c509b9d45f68436ea9fe087e37e
Source dataset
uspto-grants-2012_08
Patent number
US08242273B2

Reaction notes

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