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

HRID 44367

Reaction equation

HRID 44367 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) δ2.45 (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-31dbe6461de143a3a798065fdbe430cf
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Linked notes

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