Nitrogen → 5-(3-Fluoro-4-methoxyphenyl)pyrimidin-2-amine

HRID 1993352Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].I[C:14]1[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+].N#N.[OH-].[Na+]>O.CCO.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

Conditions

Temperature: 80 °C

Procedure

In a 500 mL round bottom flask under N2, 3-fluoro-4-methoxyphenylboronic acid (5.0 g, 29.4 mmol) and 5-iodopyrimidin-2-amine (5.5 g, 24.9 mmol) were mixed. Toluene (100 mL), EtOH (40 mL) and H2O (20 mL) were added, followed by the addition of Na2CO3 (3.0 g, 24.2 mmol). A stream of N2 was bubbled through the mixture for 5 min before the catalyst Pd(PPh)4 (0.30 g, 0.26 mmol) was added. The mixture was heated at 80° C. under N2 for 20 h whereby it was cooled to RT. A solution of NaOH (5 N, 10 mL) was added to the mixture and stirring was continued for 10 min. The mixture was filtered and the solid was washed with H2O (3×10 mL), followed by a mixture of hexanes—EtOAc (1:1, 30 mL). The solid was dried in the air to give the title compound. MS (ESI pos. ion) m/z: 220. Calc'd for C11H10FN3O: 219.08.

Workup

additionwas added
temperaturewas cooled to RT
filtrationThe mixture was filtered
washthe solid was washed with H2O (3×10 mL)
additionfollowed by a mixture of hexanes—EtOAc (1:1, 30 mL)
customThe solid was dried in the air

Sources & evidence

ORD record: ord-36f177f8d6134bff8661a6d08b1dfa61
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652009B2

Reaction notes

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