Triphenylphosphine → 5-[3-Fluoro-2'-(pyrimidin-2-ylsulfanyl)biphenyl-4-yl]pyrazin-2-amine hydrochloride

HRID 1523845Notes

Reaction equation

HRID 1523845 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][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)=[N:6][CH:7]=1.[Cl:22][C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1.CCN(C(C)C)C(C)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C>[ClH:22].[F:14][C:13]1[CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:21][C:23]2[N:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH:10]=[CH:9][C:8]=1[C:5]1[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 744042-ChloropyrimidineHCID 81531DiisopropylethylamineHCID 1364991434'-(5-Aminopyrazin-2-yl)-5'-fluorobiphenyl-2-thiol

Product 1

HCID 903135545-[3-Fluoro-2'-(pyrimidin-2-ylsulfanyl)biphenyl-4-yl]pyrazin-2-amine hydrochlorideYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-(5-aminopyrazin-2-yl)-5′-fluorobiphenyl-2-thiol (400 mg, 1.34 mmol) and 2-chloropyrimidine (167 mg, 1.47 mmol) in DMF (8 mL) were added DIPEA (345 mg, 2.68 mmol) and Ph3P (351 mg, 1.34 mmol) and the resultant mixture heated at 80° Celsius for 1 hour under a N2 atmosphere for 15 h. The mixture was cooled to rt, concentrated to dryness and the residue subjected to FCC to give the title compound (350 mg, 68%). MS (ESI): mass calcd. for C20H14FN5S.HCl, 375.10; m/z found, 376.0 [M+H]+. 1H NMR (300 MHz, CD3OD) δ 8.42 (d, J=4.9, 2H), 8.33-8.28 (m, 1H), 8.03 (d, J=1.4, 1H), 7.79-7.69 (m, 2H), 7.60-7.53 (m, 1H), 7.51-7.43 (m, 2H), 7.21 (dd, J=8.0, 1.7, 1H), 7.15 (dd, J=12.3, 1.6, 1H), 7.06 (m, 1H).

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-33af77e042074f759901c31ef3cf3e58
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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