Potassium Carbonate → HCID 58635342, compound

HRID 1351609Notes

Reaction equation

HRID 1351609 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][NH:19][C:20]3[N:25]=[CH:24][C:23]([C:26]#[C:27][Si](C)(C)C)=[CH:22][N:21]=3)[CH2:14][CH2:13]2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:26]([C:23]1[CH:24]=[N:25][C:20]([NH:19][CH2:18][CH:15]2[CH2:16][CH2:17][N:12]([C:10]([C@@H:8]3[CH2:9][C@H:7]3[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:11])[CH2:13][CH2:14]2)=[N:21][CH:22]=1)#[CH:27]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58635322HCID 58635322, compound

Product 1

HCID 58635342HCID 58635342, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-[(1-{[(1R,2R)-2-phenylcyclopropyl]carbonyl}piperidin-4-yl)methyl]-5-[(trimethylsilyl)ethynyl]pyrimidin-2-amine (EXAMPLE 154) (0.200 g, 0.462 mmol) and potassium carbonate (0.128 g, 0.924 mmol) in methanol (3 mL) was stirred at RT for 0.5 h. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate (50 mL), washed with water (20 mL), and brine (10 mL), then dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel 60 (35 g), eluting with 10:1-20:89-70 CH2Cl2:2-propanol:hexane to give the title compound. M.S. (M+1): 361.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate (50 mL)
  3. washwashed with water (20 mL), and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel 60 (35 g)
  8. washeluting with 10:1-20:89-70 CH2Cl2

Sources & evidence

ORD record
ord-a13f48b639bb47ec91197e755c24c47c
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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