Aniline → 4-(4-Amino-6-methylthieno[2,3-d]pyrimidin-5-yl)-n-phenylbenzamide

HRID 227612Notes

Reaction equation

HRID 227612 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=3)=[C:9]([CH3:20])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH:21]1[CH:22]=[CH:23][C:24]2N(O)N=[N:27][C:25]=2[CH:26]=1.NC1C=CC=CC=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([NH:27][C:25]4[CH:26]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[O:17])=[CH:18][CH:19]=3)=[C:9]([CH3:20])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 5

HCID 6115AnilineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117161604-(4-Amino-6-methylthieno[2,3-d]pyrimidin-5-yl)benzoic acid

Product 1

HCID 690584534-(4-Amino-6-methylthieno[2,3-d]pyrimidin-5-yl)-n-phenylbenzamideYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of Example 66B (89 mg, 0.31 mmol) and HOBT (46 mg, 0.35 mmol) in DMF (4 mL) at room temperature was treated with aniline (0.029 mL, 0.31 mmol), NMM (0.086 mL, 0.78 mmol) and EDC.HCl (66 mg, 0.34 mmol), stirred overnight, and partitioned between water and ethyl acetate. The aqueous phase was extracted three times with ethyl acetate and the combined organic extracts ware washed with water, and brine, dried (Na2SO4), filtered, and concentrated to a volume of about 3 mL. The product was treated with hexanes and the resulting precipitate was collected by filtration to provide 84 mg (75%) of the desired product. MS(ESI(+)) m/e 361 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 10.40 (s, 1H); 8.30 (s, 1H); 8.12 (d, J=8.4 Hz, 2H); 7.80 (d, J=7.5 Hz, 2H); 7.58 (d, J=8.4 Hz, 2H); 7.37 (t, J=7.5 Hz, 2H); 7.12 (t, J=7.5 Hz, 1H); 2.32 (s, 3H); Anal. Calcd. for C20H16N4OS.0.1C4H8O2: C, 66.36; H, 4.59; N, 15.17. Found: 66.07; H, 4.76; N, 15.32.

Workup

  1. custompartitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted three times with ethyl acetate
  3. washthe combined organic extracts ware washed with water, and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a volume of about 3 mL
  7. additionThe product was treated with hexanes
  8. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-0e9fdb60390a4056b604d7f11d097822
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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