6-[2-[[6-(2-tert-butylsilyloxypropan-2-yl)-3-pyridinyl]amino]pyrimidin-4-yl]-3-[(3S)-3-fluoropyrrolidin-1-yl]pyridine-2-carbonitrile → 3-((S)-3-Fluoro-pyrrolidin-1-yl)-6-[2-(6-hydroxymethyl-pyridin-3-ylamino)-pyrimidin-4-yl]-pyridine-2-carbonitrile

HRID 55898Notes

Reaction equation

HRID 55898 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15]2[N:20]=[C:19]([C:21]3[N:26]=[C:25]([C:27]#[N:28])[C:24]([N:29]4[CH2:33][CH2:32][C@H:31]([F:34])[CH2:30]4)=[CH:23][CH:22]=3)[CH:18]=[CH:17][N:16]=2)=[CH:10][CH:9]=1)(C)(C)C>Cl.CC#N>[F:34][C@H:31]1[CH2:32][CH2:33][N:29]([C:24]2[C:25]([C:27]#[N:28])=[N:26][C:21]([C:19]3[CH:18]=[CH:17][N:16]=[C:15]([NH:14][C:11]4[CH:12]=[N:13][C:8]([CH2:7][OH:6])=[CH:9][CH:10]=4)[N:20]=3)=[CH:22][CH:23]=2)[CH2:30]1

Participants

3

Reactant 1

HCID 1317368806-[2-[[6-(2-tert-butylsilyloxypropan-2-yl)-3-pyridinyl]amino]pyrimidin-4-yl]-3-[(3S)-3-fluoropyrrolidin-1-yl]pyridine-2-carbonitrile

Product 1

HCID 903695443-((S)-3-Fluoro-pyrrolidin-1-yl)-6-[2-(6-hydroxymethyl-pyridin-3-ylamino)-pyrimidin-4-yl]-pyridine-2-carbonitrileYield 79%

Reagents, catalysts & solvents 1

HCID 22261314Acetonitrile--hydrogen chloride (1/1)Solvent

Procedure

Compound 80 (252 mg, 0.5 mmol) was dissolved in 1:1 2 M HCl-MeCN and the reaction mixture stirred at rt for 5 hours. The solvent was removed in vacuo and the residue triturated with 9:1 EtOAc-MeOH to afford the title compound (152 mg, 79%) as a dark yellow solid; LCMS, Rt=2.40 min (MeOH-FA method), m/z 392 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue triturated with 9:1 EtOAc-MeOH

Sources & evidence

ORD record
ord-f888b70187c44de0bd12c1affa653ba4
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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