Triphenylphosphine → 5-(3-Fluoro-6'-(pyrimidin-2-ylthio)biphenyl-4-yl)pyrimidin-2-amine

HRID 1524129Notes

Reaction equation

HRID 1524129 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([C:15]3[C:16]([SH:21])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:10][CH:9]=2)=[CH:4][N:3]=1.Cl[C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C>[F:14][C:13]1[CH:12]=[C:11]([C:15]2[C:16]([S:21][C:23]3[N:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:10]=[CH:9][C:8]=1[C:5]1[CH:6]=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 744042-ChloropyrimidineHCID 903131044'-(2-Aminopyrimidin-5-yl)-5'-fluorobiphenyl-2-thiol

Product 1

HCID 903129935-(3-Fluoro-6'-(pyrimidin-2-ylthio)biphenyl-4-yl)pyrimidin-2-amineYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4′-(2-aminopyrimidin-5-yl)-5′-fluorobiphenyl-2-thiol (300 mg, 1.00 mmol), 2-chloropyrimidine (229 mg, 2.00 mmol), PPh3 (262 mg, 1.00 mmol) and TEA (0.38 mL) in DMF (10 mL) was stirred at 120° C. under a N2 atmosphere over-night. The reaction mixture was then cooled to rt, concentrated to dryness, and the residue subjected to FCC purification to give the title compound (170 mg, 45%). MS (ESI): mass calcd. for C20H14FN5S, 375.10; m/z found, 375.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.66 (s, 2H), 8.56 (d, J=4.9, 2H), 7.79-7.73 (m, 1H), 7.63-7.56 (m, 2H), 7.55-7.48 (m, 2H), 7.33-7.24 (m, 2H), 7.21 (t, J=4.9, 1H), 6.23 (s, 2H).

Workup

  1. concentrationconcentrated to dryness
  2. customthe residue subjected to FCC purification

Sources & evidence

ORD record
ord-97bbc41690d945f4950d2799ccc42ce2
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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