Butyl iodide → 6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinyl-pyrimidine-4-carboxylic acid butyl ester

HRID 506479Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=[C:4]([C:18]([OH:20])=[O:19])[C:3]=1[CH:21]=[CH2:22].I[CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[Li+].[Li+]>CN(C=O)C>[CH2:24]([O:19][C:18]([C:4]1[C:3]([CH:21]=[CH2:22])=[C:2]([NH2:1])[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=1)=[O:20])[CH2:25][CH2:26][CH3:27]

Participants

Conditions

Temperature: 60 °C

Procedure

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinyl-pyrimidine-4-carboxylic acid (0.150 g, 0.46 mmol), iodobutane (0.111 g, 0.60 mmol), and lithium carbonate (0.044 g, 0.6 mmol) were combined in DMF (1.5 mL) and heated at 60° C. overnight. The cooled reaction mixture was concentrated and partitioned between ethyl acetate and water. The organic phase was dried and concentrated. The product was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient) to yield the title compound (0.092 g, 52.3% yield): 1H NMR (CDCl3) δ 7.65 (dd, 1H), 7.19 (dd, 1H), 7.75 (dd, 1H), 5.62-5.67 (m, 2H), 5.35 (br s, 2H), 4.34 (t, 3H), 3.99 (dd, 3H), 1.74 (m, 2H), 1.45 (m, 2H), 0.97 (t, 3H).

Workup

customThe cooled reaction mixture
concentrationwas concentrated
custompartitioned between ethyl acetate and water
customThe organic phase was dried
concentrationconcentrated
customThe product was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient)

Sources & evidence

ORD record: ord-29f11c222e294825a58f8f2c83b37cc0
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786044B2

Reaction notes

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