Potassium Carbonate → HCID 89629975, compound

HRID 882126Notes

Reaction equation

HRID 882126 reaction equation
[Cl:1][C:2]1[N:6]=[C:5]([NH:7][C:8]2[CH:9]=[C:10]([C:14]3[C:15]4[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:20](COCC[Si](C)(C)C)[C:16]=4[N:17]=[CH:18][N:19]=3)[CH:11]=[CH:12][CH:13]=2)[S:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[N:6]=[C:5]([NH:7][C:8]2[CH:9]=[C:10]([C:14]3[C:15]4[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][NH:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH:11]=[CH:12][CH:13]=2)[S:4][N:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 131732643HCID 131732643, compound

Product 1

HCID 89629975HCID 89629975, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ethyl 4-{3-[(3-chloro-1,2,4-thiadiazol-5-yl)amino]phenyl}-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (75 mg, 0.14 mmol) in TFA (1.0 mL) was stirred for 1 hour. The reaction mixture was then concentrated under reduced pressure and the residue dissolved in ethyl acetate (2.0 mL). Potassium carbonate (2.0 mL, 4.0 mmol) was added and the reaction mixture was allowed to stir for 1 hour. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (×3). The combined organic fractions were washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by MPLC (0-10% methanol-dichloromethane) gave ethyl 4-{3-[(3-chloro-1,2,4-thiadiazol-5-yl)amino]phenyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C7H14ClN6O2S [M+H]+: 401, found 401. 1H NMR (600 MHz, DMSO-D6) δ 13.0 (s, 1H), 11.4 (s, 1H), 8.94 (s, 1H), 8.35 (s, 1H), 7.81 (s, 1H), 7.63 (d, 1H, J 7.63 Hz), 7.53 (t, 1H, J=7.62 Hz), 7.39 (d, 1H, J=7.63 Hz), 3.85 (q, 2H, J=7.04 Hz), 0.85 (t, 3H, J=7.04 Hz).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate (2.0 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (×3)
  5. washThe combined organic fractions were washed with water
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification of the residue by MPLC (0-10% methanol-dichloromethane)

Sources & evidence

ORD record
ord-93a648b5548044e5b19fc3fb483499c4
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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