5-(4-Aminophenyl)-6-ethylthieno[2,3-d]pyrimidin-4-amine → HCID 69057144, compound

HRID 227634Notes

Reaction equation

HRID 227634 reaction equation
[NH2:1][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[CH2:18][CH3:19])=[CH:4][CH:3]=1.[O:20]([C:22]#[N:23])[Na]>O.C(O)(=O)C>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:22]([NH2:23])=[O:20])=[CH:7][CH:6]=3)=[C:9]([CH2:18][CH3:19])[S:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

5

Reactant 2

HCID 690614255-(4-Aminophenyl)-6-ethylthieno[2,3-d]pyrimidin-4-amineHCID 178418852HCID 178418852, compound

Product 1

HCID 69057144HCID 69057144, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of Example 78A (0.27 g, 1 mmol) and NaOCN (0.13 g, 2 mmol) in water (1.5 mL) and acetic acid (1.5 mL) was stirred overnight at room temperature and partitioned between water and ethyl acetate. The organic extract was washed with saturated aqueous NaHCO3 and brine, dried (MgSO4), filtered, and concentrated to provide 0.3 g of the desired product. MS (ESI(+)) m/e 314 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 1.15 (t, J=7.46 Hz, 3H); 2.63 (q, J=7.57 Hz, 2H); 5.94 (m, 2H); 7.24 (d, J=8.48 Hz, 2H); 7.56 (d, J=8.48 Hz, 2H); 8.25 (s, 1H); 8.75 (s, 1H).

Workup

  1. custompartitioned between water and ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b4139baae0084d78812ffff666d0009d
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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