1,2-Dimethoxyethane → 2-Methyl-5-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)-phenylamine

HRID 2262143Notes

Reaction equation

HRID 2262143 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[CH3:24].COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:24][C:23]1[CH:22]=[CH:21][C:20]([C:2]2[N:3]=[C:4]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]3[S:10][CH:9]=[CH:8][C:6]=3[N:7]=2)=[CH:19][C:18]=1[NH2:17]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2737803(3-Amino-4-methylphenyl)boronic acidHCID 202849712-Chloro-4-(morpholin-4-yl)thieno(3,2-d)pyrimidine

Product 1

HCID 671889492-Methyl-5-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)-phenylamineYield 94.4%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 4 (772 mg), 3-amino-4-methylbenzeneboronic acid (502 mg), DME (10 mL), water (5 mL), sodium carbonate (640 mg) and PdCl2(PPh3)2 (100 mg) was heated to reflux for 16 hours. The reaction mixture was then cooled, diluted with ethyl acetate, and reduced in vacuo. The residue was purified using flash chromatography to yield 2-methyl-5-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)-phenylamine (930 mg).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. temperatureThe reaction mixture was then cooled
  4. customThe residue was purified

Sources & evidence

ORD record
ord-c50090a51c214c7a8ccdc68a8b829fd6
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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