Hydrochloric Acid → (E)-6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-(2-(trihydroxysilyl)vinyl)pyrimidine-4-carboxylic acid

HRID 244315Notes

Reaction equation

HRID 244315 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][CH3:18])[C:11]=2[F:19])[N:7]=[C:6]([C:20]([O:22]C)=[O:21])[C:5]=1/[CH:24]=[CH:25]/[Si:26]([O:33]CC)([O:30]CC)[O:27]CC.CO.Cl>O1CCCC1>[NH2:3][C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][CH3:18])[C:11]=2[F:19])[N:7]=[C:6]([C:20]([OH:22])=[O:21])[C:5]=1/[CH:24]=[CH:25]/[Si:26]([OH:33])([OH:30])[OH:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 70497970(E)-methyl 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-(2-(triethoxysilyl)vinyl)pyrimidine-4-carboxylate

Product 1

HCID 70498437(E)-6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-(2-(trihydroxysilyl)vinyl)pyrimidine-4-carboxylic acidYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2M aqueous solution of sodium hydroxide (150 μL, 0.31 mmol, 1.05 equiv) was added to a stirred solution of (E)-methyl 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-(2-(triethoxysilyl)vinyl)pyrimidine-4-carboxylate (145 mg, 0.29 mmol, 1.0 equiv) in 3:1 methanol:tetrahydrofuran (4.0 mL) at room temperature. The homogeneous yellow solution was stirred at room temperature for 20 h. The reaction mixture was adjusted to pH 4 using concentrated hydrochloric acid and concentrated under vacuum. The residue was slurried in water and vacuum filtered to provide the title compound as a tan powder (95 mg, 81% yield): mp 220-250° C. (decomposition); IR (thin film) 3323 (m), 3195 (m), 2944 (w), 1603 (s), 1534 (s) cm−1; 1H NMR (400 MHz, DMSO-d6) δ 7.56-7.76 (m, 1H), 6.59-7.52 (m, 4H), 3.93 (br s, 3H); ESIMS m/z 402 [(M+H)+].

Workup

  1. customat room temperature
  2. concentrationconcentrated under vacuum
  3. filtrationvacuum filtered

Sources & evidence

ORD record
ord-a62f06a845a7402c9ef8a2685da269bf
Source dataset
uspto-grants-2014_02
Patent number
US08658568B2

Reaction notes

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