Sodium Carbonate → N-[2-amino-6-(4-ethoxyphenyl)-4-pyrimidinyl]-N-[3-fluoro-4-(4-pyridinylsulfanyl)phenyl]amine

HRID 583822Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:11]([F:22])[CH:10]=2)[CH:5]=[C:4](Cl)[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:30]([O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)[CH3:31]>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:11]([F:22])[CH:10]=2)[CH:5]=[C:4]([C:36]2[CH:37]=[CH:38][C:33]([O:32][CH2:30][CH3:31])=[CH:34][CH:35]=2)[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of N-(2-amino-6-chloro-4-pyrimidinyl)-N-[3-fluoro-4-(4-pyridinylsulfanyl)phenyl]amine from step 1 in toluene (2 mL) in ethanol (1 mL) was treated with aqueous sodium carbonate solution (2M, 0.5 mL). The mixture was then treated with 4-ethoxyphenylboronic acid (0.36 mmol), tetrakis(triphenylphosphine)-palladium (0.009 mmol), and allowed to stir at 120° C. under argon overnight. At this time, the solvents were removed at reduced pressure and the residue was purified by preparative silica gel with 3% MeOH in CH2Cl2 to afford the desired product as a white solid (21 mg).

Workup

customAt this time, the solvents were removed at reduced pressure
customthe residue was purified by preparative silica gel with 3% MeOH in CH2Cl2

Sources & evidence

ORD record: ord-6d4a5e9c22ad4ee1b561dd8257329d74
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924290B2

Reaction notes

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