Dimethylformamide → HCID 58942254, compound

HRID 2092330Notes

Reaction equation

HRID 2092330 reaction equation
[CH3:1][NH:2][C:3]1[N:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8](B3OC(C)(C)C(C)(C)O3)[CH:9]=2)[N:4]=1.I[C:23]1[C:31]2[S:30][N:29]=[C:28]([NH2:32])[C:27]=2[CH:26]=[CH:25][C:24]=1[CH3:33].C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>O.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>[NH2:32][C:28]1[C:27]2[CH:26]=[CH:25][C:24]([CH3:33])=[C:23]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[N:4]=[C:3]([NH:2][CH3:1])[N:12]=[CH:11]4)[C:31]=2[S:30][N:29]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 16086139N-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)quinazolin-2-amineHCID 584664897-Iodo-6-methylbenzo[d]isothiazol-3-amine

Product 1

HCID 58942254HCID 58942254, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
150 °C

Procedure

N-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine (0.42 g, 1.5 mmol), 7-iodo-6-methylbenzo[d]isothiazol-3-amine (0.39 g, 1.3 mmol), dichlorobis(triphenyl-phosphine)palladium (II) (0.047 g, 0.067 mmol) and sodium carbonate (0.14 g, 1.3 mmol) were all placed in a clear microwave vial along with 5 ml of 9:1 DMF:water. The vial was capped and heated in a Personal Chemistry SmithSynthesizer to 150° C. for 10 minutes. The reaction was diluted with water and extracted with EtAOc. The organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 50 to 100% EtOAc in hexanes. The clean fractions were triturated with warm ether and the solid collected by suction filtration and dried to give 6-(3-amino-6-methylbenzo[d]isothiazol-7-yl)-N-methylquinazolin-2-amine as a tan solid. MS(M+H)+ 322.

Workup

  1. customThe vial was capped
  2. extractionextracted with EtAOc
  3. washThe organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. custompurified by column chromatography on silica gel using a gradient of 50 to 100% EtOAc in hexanes
  6. customThe clean fractions were triturated with warm ether
  7. filtrationthe solid collected by suction filtration
  8. customdried

Sources & evidence

ORD record
ord-3a1149ce03194f9bbaa2c2323e2b0af1
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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