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5-(Trimethylstannyl)nicotinonitrile → (S)-5-{6-chloro-2-[1-(4-fluorophenyl)ethylamino]pyrimidin-4-yl}nicotinonitrile

HRID 1187709
Notes
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Reaction equation

HRID 1187709 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[N:3]=1.C[Sn](C)(C)[C:21]1[CH:22]=[N:23][CH:24]=[C:25]([CH:28]=1)[C:26]#[N:27]>[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[Cl:8][C:6]1[N:5]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])[N:3]=[C:2]([C:21]2[CH:22]=[N:23][CH:24]=[C:25]([CH:28]=2)[C:26]#[N:27])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 186990455-(Trimethylstannyl)nicotinonitrileHCID 86659372(S)-4,6-Dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidin-2-amine

Product 1

HCID 86659396(S)-5-{6-chloro-2-[1-(4-fluorophenyl)ethylamino]pyrimidin-4-yl}nicotinonitrileYield 25.1%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalyst
HCID 178418397
HCID 178418397, compound
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

187 mg of (S)-4,6-dichloro-N-[1-(4-fluorophenyl)ethyl]pyrimidine-2-amine (Reference Example 1), 175 mg of 5-(trimethylstannyl)nicotinonitrile, 25 mg of copper iodide and 75 mg of tetrakis(triphenylphosphine)palladium were added in turn to 3 ml of degassed toluene, and the mixture was stirred at 110° C. for 17 hours under argon atmosphere. The reaction solution was purified by silica gel column chromatography to obtain 58 mg of (S)-5-{6-chloro-2-[1-(4-fluorophenyl)ethylamino]pyrimidin 4-yl}nicotinonitrile as colorless oil.

Workup

  1. customThe reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ddd5f293936247a29ded7aaed3380749
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673891B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes