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Sodium Carbonate → Methyl 3-(7-(3-(methylsulfonyl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoate

HRID 1410046
Notes
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Reaction equation

HRID 1410046 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:30]2[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=2)[C:33]([O:35][CH3:36])=[O:34])O1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>O.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>[CH3:21][S:18]([C:14]1[CH:13]=[C:12]([NH:11][C:4]2[C:5]3[N:10]=[CH:9][S:8][C:6]=3[N:7]=[C:2]([C:30]3[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=3)[C:33]([O:35][CH3:36])=[O:34])[N:3]=2)[CH:17]=[CH:16][CH:15]=1)(=[O:20])=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27346513-Methoxycarbonylphenylboronic acid pinacol esterHCID 866717835-chloro-N-(3-(methylsulfonyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine

Product 1

HCID 66549139Methyl 3-(7-(3-(methylsulfonyl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoateYield 58%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Procedure

Under N2 atmosphere, 5-chloro-N-(3-(methylsulfonyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (200 mg, 0.59 mmol), methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (183 mg, 0.7 mmol), Pd(PPh3)4 (30 mg, 0.026 mmol) and Na2CO3 (127 mg, 1.2 mmol) in 5 mL of water was added into the mixture solvent of 5 mL of water and 50 mL of 1,4-dioxane. The mixture was stirred at reflux for 18 hours. The solvent was removed under reduce pressure and the residue was purified by silica gel chromatography, eluting with petroleum ether and ethyl acetate (3:1) to give methyl 3-(7-(3-(methylsulfonyl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoate (150 mg, 58%) as a yellow sold. 1H NMR (300 MHz, DMSO): δ 10.76 (s, 1H), 9.45 (s, 1H), 8.99-8.98 (m, 1H), 8.93 (s, 1H), 8.73 (d, 1H, J=7.8 Hz), 8.21-8.18 (m, 1H), 8.09 (d, 1H, J=7.8 Hz), 7.69-7.65 (m, 3H), 3.91 (s, 3H), 3.26 (s, 3H). LC-MS: 441 [M+H]+, 903 [2M+Na]+, 439 [M−H]−, tR=1.61 min. HPLC: 98.78% at 214 nm, 97.72% at 254 nm, tR=8.14 min.

Workup

  1. temperatureat reflux for 18 hours
  2. customThe solvent was removed
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with petroleum ether and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-c3f65baac0054296a32d6b2df2c03f53
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921383B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes