Ethyl cyanoacetate → Ethyl 5-amino-2-methylthio-4-(3-n-octyloxyphenyl)-thieno[2,3-d]-pyrimidine-6-carboxylate

HRID 413967Notes

Reaction equation

HRID 413967 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].[CH2:11]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:28]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])#[N:29].O=P(Cl)(Cl)Cl.[SH:41][CH2:42][C:43](OCC)=O>ClCCl.CO>[NH2:29][C:28]1[C:43]2[C:23]([C:22]3[CH:25]=[CH:26][CH:27]=[C:20]([O:19][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:21]=3)=[N:9][C:8]([S:7][CH3:6])=[N:10][C:42]=2[S:41][C:30]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

7

Reactant 5

HCID 7764Ethyl cyanoacetateHCID 12185Ethyl ThioglycolateHCID 24813Phosphorus oxychlorideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 138033443-(Octyloxy)benzaldehyde

Product 1

HCID 22597564Ethyl 5-amino-2-methylthio-4-(3-n-octyloxyphenyl)-thieno[2,3-d]-pyrimidine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Cyclization of S-methylisothiourea sulfate (139 mg), 3-n-octyloxybenzaldehyde (338 mg) and ethyl cyanoacetate (112 μl), treatment of the product with POCl3 and subsequent reaction with ethyl 2-mercaptoacetate were performed according to the methods described in example 1. The pure title compound was obtained after chromatography on silicagel in dichloromethane/methanol=100/0 (v/v)→90/10 (v/v) as eluent.

Sources & evidence

ORD record
ord-0a669b9319404f23a950862aa484ad30
Source dataset
uspto-grants-2003_05
Patent number
US06569863B1

Reaction notes

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