Formaldehyde → HCID 53390142, compound

HRID 1045780Notes

Reaction equation

HRID 1045780 reaction equation
Cl.[N:2]1([C:8]2[N:13]3[N:14]=[N:15][N:16]=[C:12]3[C:11]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)=[CH:10][N:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:22](Cl)Cl.CO.C=O>C([O-])(O)=O.[Na+]>[CH3:22][N:5]1[CH2:4][CH2:3][N:2]([C:8]2[N:13]3[N:14]=[N:15][N:16]=[C:12]3[C:11]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)=[CH:10][N:9]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 6344DichloromethaneHCID 67394757HCID 67394757, compound

Product 1

HCID 53390142HCID 53390142, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A 100 mL round bottom flask was charged with 5-(piperazin-1-yl)-8-(thiophen-2-yl)tetrazolo[1,5-c]pyrimidine hydrochloride (0.16 g, 0.49 mmol), CH2Cl2 (20 mL), methanol (10 mL), 40% aqueous formaldehyde (2 mL) and NaBH3(CN) (0.1 g, 1.7 mmol). The resulting solution was stirred at room temperature for 0.5 h. Work-up: the reaction mixture was diluted with saturated aqueous NaHCO3 and extracted with CH2Cl2 (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 1-10% MeOH in CH2Cl2 to afford 24 mg (16%) of the product as a white solid. 1H NMR (300 MHz, CD3OD) δ: 8.55 (s, 1H), 7.42 (dd, J=5.1, 1.2 Hz, 1H), 7.39 (dd, J=3.6, 1.2 Hz, 1H), 7.08 (dd, J=5.1, 3.6 Hz, 1H), 3.70-3.40 (br, 4H), 3.30-3.10 (br, 4H), 2.96 (s, 3H). MS m/z: 302 (M+H+).

Workup

  1. extractionextracted with CH2Cl2 (50 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel with 1-10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-1c53b30e7411450f879e34c54f331339
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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