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Triethylamine → 3-{2-[(Quinolin-4-ylmethyl)amino]ethyl}-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one

HRID 912721
Notes
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Reaction equation

HRID 912721 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][N:11]1[C:19]2[N:18]=[CH:17][NH:16][C:15]=2[C:14](=[O:20])[NH:13][C:12]1=[S:21].C(N(CC)CC)C.[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH:39]=O)=[CH:31][CH:30]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH2:39][NH:8][CH2:9][CH2:10][N:11]2[C:19]3[N:18]=[CH:17][NH:16][C:15]=3[C:14](=[O:20])[NH:13][C:12]2=[S:21])=[CH:31][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 780724-QuinolinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 866311443-(2-Aminoethyl)-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one trifluoroacetate

Product 1

HCID 248556323-{2-[(Quinolin-4-ylmethyl)amino]ethyl}-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-oneYield 29.3%

Reagents, catalysts & solvents

2
HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

3-(2-Aminoethyl)-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one trifluoroacetate (98 mg, 0.3 mmol, obtained from Example 26(b)) and triethylamine (0.043 mL, 0.31 mmol) was stirred in dry methanol for 15 min. 4-Quinoline carboxaldehyde (47 mg, 0.3 mmol) and acetic acid (3 drops) were added and the mixture was stirred o.n. Sodium cyanoborohydride (28 mg, 0.45 mmol) was added and the mixture was stirred for 5 h. The mixture was then concentrated and purified by preparative HPLC, giving 31 mg (29% yield) of the title compound

Workup

  1. stirringthe mixture was stirred for 5 h
  2. concentrationThe mixture was then concentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-333418bff52140bbb290a4d8ae64fd74
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08026244B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes