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tert-Butanol → N,N-diethyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-amine

HRID 22787
Notes
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Reaction equation

HRID 22787 reaction equation
Cl[C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][CH2:13][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15].[C:19](O)(C)(C)C.CCOC(C)=O>O.Cl>[CH2:14]([N:16]([CH2:17][CH3:18])[C:2]1[C:3]2[C:10]3[CH2:19][CH2:11][CH2:12][CH2:13][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1)[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8021Diethylamine2×HCID 8857Ethyl AcetateHCID 78981712-Chloro-7-thia-9,11-diazatricyclo(6.4.0.0,2,6)dodeca-1(12),2(6),8,10-tetraene

Product 1

HCID 717848N,N-diethyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 21885828
Hydrate;hydrochloride
Solvent

Procedure

To a slurry of 0.044 g 4-chloro-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine (0.196 mmol) in 1 mL of 100:1 H2O/HCl was added 0.014 g (0.02 mL, 0.106 mmol) diethylamine. The mixture was heated to reflux, and an additional 0.2 mL diethylamine and 1 mL of t-butanol were added and heated continued at reflux for an additional 1 h. TLC (20% EtOAc/80% pet ether) showed complete reaction and the 1H NMR of the isolated material was consistent with the desired product.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureheated
  4. temperatureat reflux for an additional 1 h
  5. customreaction

Sources & evidence

ORD record
ord-dcfb3b429c2544d6bb6f40646bccd630
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06849638B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes