Potassium Carbonate → MK-8189

HRID 2175405Notes

Reaction equation

HRID 2175405 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH2:7][N:8]([C:16]2[CH:21]=[C:20]([O:22][CH2:23][C@H:24]3[CH2:26][C@@H:25]3[C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=3)[N:19]=[C:18]([CH3:34])[N:17]=2)C(=O)OC(C)(C)C)=[N:4][N:3]=1.C([O-])([O-])=O.[K+].[K+]>CO.CCOC(C)=O>[CH3:34][C:18]1[N:17]=[C:16]([NH:8][CH2:7][C:5]2[S:6][C:2]([CH3:1])=[N:3][N:4]=2)[CH:21]=[C:20]([O:22][CH2:23][C@H:24]2[CH2:26][C@@H:25]2[C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=2)[N:19]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86729565tert-Butyl ((5-methyl-1,3,4-thiadiazol-2-yl)methyl)(2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyrimidin-4-yl)carbamate

Product 1

HCID 71271414MK-8189Yield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-2 (51.0 mg, 0.11 mmol) in MeOH (0.53 mL) was added K2CO3 (17.5 mg, 0.13 mmol). The resulted suspension was stirred at 70° C. for 2 hour. The mixture was diluted with EtOAc, and then extracted with 1N HCl. The aqueous layer was basified with 5N NaOH and extracted with DCM three times. The combined DCM layers were dried over Na2SO4 and concentrated to give 2-3″ as an off white solid (29 mg, 72%). MS (M+H)+: observed=383.1654, calculated=383.1649. 1H NMR (400 MHz, DMSO-d6): δ 8.22 (s, 1H), 7.82 (br t, J=5.0 Hz, 1H), 7.45 (d, J=7.9 Hz, 1H), 7.17 (d, J=7.7 Hz, 1H), 5.64 (s, 1H), 4.76 (d, J=5.0 Hz, 2H), 4.23 (m, 1H), 4.14 (m, 1H), 2.65 (s, 3H), 2.31 (s, 3H), 2.22 (s, 3H), 2.09 (m, 1H), 1.71 (m, 1H), 1.12 (m, 1H), 0.98 (m, 1H)

Workup

  1. extractionextracted with 1N HCl
  2. extractionextracted with DCM three times
  3. dry with materialThe combined DCM layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0fc85cc44ec247d1a5acf0d025f95334
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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