Dimethylformamide → 1-[4-(4-Amino-6-methylthieno[2,3-d]pyrimidin-5-yl)phenyl]-3-phenylacetone

HRID 227630Notes

Reaction equation

HRID 227630 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[S:10][C:9]=2[CH3:18])=[CH:4][CH:3]=1.[C:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)#[C:20][CH3:21].C(NCC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C=[O:56])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.[Cu]I>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH2:21][C:20]([CH2:19][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:56])=[CH:3][CH:4]=3)=[C:9]([CH3:18])[S:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 69601MethylphenylacetyleneHCID 116311235-(4-Bromophenyl)-6-methylthieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 690608361-[4-(4-Amino-6-methylthieno[2,3-d]pyrimidin-5-yl)phenyl]-3-phenylacetone

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of Example 66A (100 mg, 0.31 mmol), 2-propynylbenzene (0.042 mL, 0.34 mmol), Pd(PPh3)2Cl2 (11 mg, 0.016 mmol), CuI (3 mg, 0.016 mmol), diethylamine (0.48 mL, 4.68 mmol), and triphenylphosphine (16 mg, 0.062 mmol) in DMF (0.5 mL) in capped 5 mL vial was stirred while heating to 120° C. for 25 minutes in a Smith Synthesizer microwave at 300 W. The mixture cooled using 40 psi pressurized air, diluted with water, and extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by silica gel chromatography with ethyl acetate to provide 38 mg of the desired product. MS (ESI(+)) m/e 374 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 2.28 (s, 3H); 3.91 (s, 2H); 3.97 (s, 2H); 7.16-7.36 (m, 9H); 8.27 (s, 1H).

Workup

  1. temperatureThe mixture cooled
  2. extractionextracted three times with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel chromatography with ethyl acetate

Sources & evidence

ORD record
ord-a4b3e64d0c514510b08441e836c1b211
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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