Thiourea → HCID 66557755, compound

HRID 1295476Notes

Reaction equation

HRID 1295476 reaction equation
Br[C:2]1[N:3]([CH2:12][CH2:13][CH2:14][CH3:15])[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[CH:6][N:5]=2.NC(N)=[S:18]>C(O)CCC>[NH2:11][C:8]1[N:7]=[CH:6][N:5]=[C:4]2[C:9]=1[NH:10][C:2](=[S:18])[N:3]2[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 116087198-Bromo-9-butyl-9H-purin-6-amine

Product 1

HCID 66557755HCID 66557755, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A suspension of 8-bromo-9-butyl-9H-purin-6-ylamine (0.50 g, 1.85 mmol) and thiourea (1.49 g, 19.6 mmol) in n-butanol (10 ml) was heated to reflux for 14 h. Dilution with CH2Cl2 (70 ml), washing with water and concentration afforded 6-amino-9-butyl-7,9-dihydro-purine-8-thione as a white powder (0.42 g, 1.87 mmol, 100%). 1H NMR (DMSO-d6) δ 12.35-12.25 (br. s, 1H), 8.13 (s, 1H), 6.92-6.72 (br. s., 2H), 4.09 (t, J=7.6 Hz, 2H), 1.71 (quint., J=7.5 Hz, 2H), 1.29 (sext., J=7.5 Hz, 2H), 0.87 (t, J=7.4 Hz, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 14 h
  3. washDilution with CH2Cl2 (70 ml), washing with water and concentration

Sources & evidence

ORD record
ord-e8e03b0d201d4278b0a26e093092e3dc
Source dataset
uspto-grants-2007_07
Patent number
US07241890B2

Reaction notes

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