Ammonia acetate → 5,6-Dimethyl-2-phenylthieno[2,3-d]pyrimidin-4-amine

HRID 2076982Notes

Reaction equation

HRID 2076982 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].C(O)(=O)C.[NH3:15].CCO[C:19](OCC)(OCC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCOC(C)=O>[CH3:9][C:5]1[C:6]2[C:7]([NH2:15])=[N:8][C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:1][C:2]=2[S:3][C:4]=1[CH3:10]

Participants

5

Reactant 3

HCID 12432Ammonia acetateHCID 74268Benzene, (triethoxymethyl)-HCID 2902362-Amino-4,5-dimethyl-thiophene-3-carbonitrile

Product 1

HCID 252243435,6-Dimethyl-2-phenylthieno[2,3-d]pyrimidin-4-amineYield 31%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-amino-4,5-dimethylthiophene-3-carbonitrile (152 mg, 1.0 mmol), ammonia acetate (308.3 mg, 4.0 mmol) and triethyl orthobenzoate (2.0 mL) in a sealed tube was put in a microwave at 200° C. for 20 min. After the reaction mixture was cooled to room temperature, it was diluted with EtOAc, washed with saturated NaHCO3 and H2O. The solvent was removed by vacuum and the residue was purified by preparative HPLC eluting with acetonitrile and water to give the title compound (80 mg, 31%). 1H NMR (400 MHz, CDCl3) δ 2.45 (s, 3H), 2.48 (s, 3H), 5.34 (bs, 2H), 7.46-7.43 (m, 3H), 8.4-8.38 (m, 2H). MS 256 (MH+).

Workup

  1. washwashed with saturated NaHCO3 and H2O
  2. customThe solvent was removed by vacuum
  3. customthe residue was purified by preparative HPLC
  4. washeluting with acetonitrile and water

Sources & evidence

ORD record
ord-50299aee3b424b189c54acd44f63802f
Source dataset
uspto-grants-2011_04
Patent number
US07928111B2

Reaction notes

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