Water → 5-(4-Aminophenyl)-6-methylthieno[2,3-d]pyrimidin-4-amine

HRID 227600Notes

Reaction equation

HRID 227600 reaction equation
[CH3:1][C:2]1[S:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH2:10])[C:4]=2[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1.O.[NH4+].[Cl-]>C(O)C.C1COCC1.[Fe]>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:3]2[C:4]3[C:9]([NH2:10])=[N:8][CH:7]=[N:6][C:5]=3[S:11][C:2]=2[CH3:1])=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 116162046-Methyl-5-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 65399685-(4-Aminophenyl)-6-methylthieno[2,3-d]pyrimidin-4-amineYield 110.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of Example 1D (1.01 g, 3.53 mmol) in ethanol (60 mL), THF (20 mL), and water (10 mL) was treated with NH4Cl (0.19 g, 3.53 mmol) and iron powder (1.18 g, 21.2 mmol), and stirred at 70-80° C. for 1 hour. The mixture was diluted with ethanol (40 mL) and filtered through a pad of diatomaceous earth (Celite®) while still hot. The pad was washed with ethanol and the filtrate was concentrated. The concentrate was diluted with water and extracted three times with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide 1 g of the desired product. MS (CI) m/e 257 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.23 (s, 1H); 7.01 (d, J=8.4 Hz, 2H); 6.70 (d, J=8.4 Hz, 2H); 5.39 (s, 2H); 2.27 (s, 3H); Anal. Calcd. for C13H12N4S.0.2C4H8O2.0.2H2O: C, 59.72; H, 5.08; N, 20.19. Found: 59.64; H, 4.99; N, 20.22.

Workup

  1. filtrationfiltered through a pad of diatomaceous earth (Celite®) while still hot
  2. washThe pad was washed with ethanol
  3. concentrationthe filtrate was concentrated
  4. additionThe concentrate was diluted with water
  5. extractionextracted three times with ethyl acetate
  6. washThe combined extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a21037430dad44448498ae37eaca66d6
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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