Sodium Iodide → (R)-5-(2-(1H-pyrrol-1-yl)thiazol-4-yl)-2-morpholino-6-(piperidin-3-ylamino)pyrimidin-4(3H)-one

HRID 1507495Notes

Reaction equation

HRID 1507495 reaction equation
[N:1]1([C:6]2[S:7][CH:8]=[C:9]([C:11]3[C:12]([NH:25][C@@H:26]4[CH2:31][CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]4)=[N:13][C:14]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:15][C:16]=3[O:17]C)[N:10]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[Na+].[I-].[Si](Cl)(C)(C)C>CC#N>[N:1]1([C:6]2[S:7][CH:8]=[C:9]([C:11]3[C:16](=[O:17])[NH:15][C:14]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:13][C:12]=3[NH:25][C@@H:26]3[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]3)[N:10]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 117677378(R)-tert-butyl 3-((5-(2-(1H-pyrrol-1-yl)thiazol-4-yl)-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate

Product 1

HCID 136272323(R)-5-(2-(1H-pyrrol-1-yl)thiazol-4-yl)-2-morpholino-6-(piperidin-3-ylamino)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (R)-tert-butyl 3-((5-(2-(1H-pyrrol-1-yl)thiazol-4-yl)-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate (xx) (0.08 g, 0.148 mmol) in MeCN (2.95 ml) was added NaI (0.033 g, 0.222 mmol) followed by TMS-Cl (0.028 ml, 0.222 mmol) under argon. The reaction was stirred at room temperature for 15 min., then heated to 50° C. for 2 h until the reaction was complete, monitored by LCMS. The solvent was removed and the reaction material was purified by preparative HPLC to give the title compound. MS (m/z)=428 (M+H). IRAK4 IC50=12 nM

Workup

  1. temperatureheated to 50° C. for 2 h until the reaction
  2. customThe solvent was removed
  3. customthe reaction material was purified by preparative HPLC

Sources & evidence

ORD record
ord-0f3513904d9349af90b1d52dcf51b6a3
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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