Water → 3-[7-(3,4-Dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-benzoic acid methyl ester

HRID 1409997Notes

Reaction equation

HRID 1409997 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:22][O:23][C:24](=[O:40])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:22][O:23][C:24](=[O:40])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:2]2[N:3]=[C:4]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[C:5]3[N:10]=[CH:9][S:8][C:6]=3[N:7]=2)[CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27346513-Methoxycarbonylphenylboronic acid pinacol esterHCID 715341855-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine

Product 1

HCID 683794533-[7-(3,4-Dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-benzoic acid methyl esterYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of (5-chloro-thiazolo[5,4-d]pyrimidin-7-yl)-(3,4-dimethoxy-phenyl)-amine (0.90 g, 2.79 mmol) and 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (0.95 g, 3.62 mmol) in 100 mL of 1,4-dioxane were added Na2CO3 (0.93 g, 8.8 mmol) and 5 mL of water at room temperature. Then the mixture was degassed with nitrogen for 15 minutes. Pd(PPh3)4 (0.32 g, 0.279 mmol) was added in one portion and the reaction mixture was stirred at 100° C. for 16 hours under nitrogen. The solvent was evaporated and the residue was purified by silica gel chromatography (silica gel 200-300 mesh, CH2Cl2:methanol=100:1) to give 3-[7-(3,4-dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-benzoic acid methyl ester (0.95 g, 81%) as a yellow sold. LC-MS: 423.1 [M+H]+, tR=1.68 min.

Workup

  1. customThen the mixture was degassed with nitrogen for 15 minutes
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel chromatography (silica gel 200-300 mesh, CH2Cl2:methanol=100:1)

Sources & evidence

ORD record
ord-64036bf4bfa6439498becfbb12fadfef
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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