Triethylamine → 1-benzyl-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

HRID 1098208Notes

Reaction equation

HRID 1098208 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:14]([CH:15]=O)=[C:13]([Cl:17])[N:12]=[CH:11][N:10]=1.Cl.Cl.[CH2:20]([NH:27][NH2:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH2:20]([N:27]1[C:9]2=[N:10][CH:11]=[N:12][C:13]([Cl:17])=[C:14]2[CH:15]=[N:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 146540Benzylhydrazine dihydrochlorideHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

Product 1

HCID 114250891-benzyl-4-chloro-1H-pyrazolo[3,4-d]pyrimidineYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (1.181 mL, 8.48 mmol) was added to 4,6-dichloropyrimidine-5-carbaldehyde (CAS no. 5305-40-8) (500 mg, 2.83 mmol) and benzylhydrazine dihydrochloride (CAS no. 20570-96-1) (551 mg, 2.83 mmol) in THF (15 mL) at room temperature under nitrogen. The resulting suspension was stirred at room temperature for 10 minutes and then heated at 65° C. for 50 mins. Silica was added to the reaction mixture and concentrated in vacuo. The crude product was purified by flash silica chromatography, elution gradient 20 to 50% EtOAc in isohexane to afford the product (500 mg, 72.3%). 1H NMR (400 MHz, CDCl3) 5.67 (2H, s), 7.28-7.38 (5H, m), 8.16 (1H, s), 8.79 (1H, s); m/z (ES+) (M+H)+=245; HPLC tR=2.29 min.

Workup

  1. customat room temperature
  2. temperatureheated at 65° C. for 50 mins
  3. additionSilica was added to the reaction mixture
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash silica chromatography, elution gradient 20 to 50% EtOAc in isohexane

Sources & evidence

ORD record
ord-a094f5363670419295373c8caa31bdea
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

Loading…