Potassium Carbonate → HCID 50943689, compound

HRID 1484911Notes

Reaction equation

HRID 1484911 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([NH:9][C:10]3[C:15]([C:16]#[C:17][Si](C)(C)C)=[CH:14][N:13]=[C:12]([C:22]4[S:26][C:25]([C:27]([OH:30])([CH3:29])[CH3:28])=[CH:24][CH:23]=4)[N:11]=3)[NH:6][N:5]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+]>CO>[CH:1]1([C:4]2[NH:5][N:6]=[C:7]([NH:9][C:10]3[C:15]([C:16]#[CH:17])=[CH:14][N:13]=[C:12]([C:22]4[S:26][C:25]([C:27]([OH:30])([CH3:28])[CH3:29])=[CH:24][CH:23]=4)[N:11]=3)[CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178458263HCID 178458263, compound

Product 1

HCID 50943689HCID 50943689, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(5-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-5-((trimethylsilyl)ethynyl)pyrimidin-2-yl)thiophen-2-yl)propan-2-ol (115 mg, 0.26 mmol), K2CO3 (72 mg, 0.52 mmol, 2.0 equiv.) in CH3OH (10 ml) was stirred at room temperature for 1 h. The mixture was filtered. The solid was washed with water and extracted with EtOAc. The extract was washed by brine, dried (Na2SO4), filtered and concentrated. The residue was recrystalized by ether to give compound 2-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)propan-2-ol (Compound 180) (53 mg, 55%). LC-MS (m/z)=366.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.73-0.77 (m, 2H), 0.96-1.01 (m, 2H), 1.54 (s, 6H), 1.91-1.97 (m, 1H), 4.83 (s, 1H), 5.60 (s, 1H), 6.52 (s, 1H), 7.01 (d, J=4.0 Hz, 1H), 7.69 (d, J=4.0 Hz, 1H), 8.63 (s, 1H), 8.45 (s, 1H), 8.56 (bs, 1H), 12.24 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. washThe solid was washed with water
  3. extractionextracted with EtOAc
  4. washThe extract was washed by brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystalized by ether

Sources & evidence

ORD record
ord-12cb7471dfca4b5d9abd1dc9426adc97
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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