Formamidine acetate → HCID 178468703, compound

HRID 1526500Notes

Reaction equation

HRID 1526500 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][C:5]=2[C:6]=1[C:7](OCC)=[O:8].C(O)(=O)C.[CH:25](N)=[NH:26]>C(N)=O.CCOC(C)=O>[OH:8][C:7]1[C:6]2[C:5]3[CH2:12][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:15][C:4]=3[S:3][C:2]=2[N:1]=[CH:25][N:26]=1

Participants

5

Reactant 2

HCID 160693Formamidine acetateHCID 59379278HCID 59379278, compound

Product 1

HCID 178468703HCID 178468703, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 713FormamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A solution of 3,5-diethyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3,5-dicarboxylate (8 g, 26.90 mmol, 1.00 equiv) in formamide (150 mL) was added formamidine acetate (10 g, 96.05 mmol, 3.57 equiv) at room temperature under nitrogen. The resulting solution was stirred for 4 h at 180° C. After cooling, the resulting solution was diluted with 200 mL of EtOAc, washed with water and brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4) give the desired ethyl 4-hydroxy-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine-6-carboxylate (4.1 g, 55%) as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5e66a047b7344f40ae6dde4e0b0024ee
Source dataset
uspto-grants-2015_07
Patent number
US09085586B2

Reaction notes

Loading…