Ethyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate → 5-methyl-4-oxo-N-[(3-{[2-(1H-1,2,4-triazol-3-yloxy)ethyl]oxy}phenyl)methyl]-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide

HRID 606385Notes

Reaction equation

HRID 606385 reaction equation
O=C1C2C(=CC=CC=2)N=C(C(OCC)=O)N1.[CH3:17][C:18]1[C:26]2[C:25](=[O:27])[NH:24][C:23]([C:28]([O:30]CC)=O)=[N:22][C:21]=2[S:20][CH:19]=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)N2C=NC(CCCOC3C=C(CN)C=CN=3)=N2)C=CC=CC=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:76]2[CH:80]=[N:79][C:78]([O:81][CH2:82][CH2:83][O:84][C:85]3[CH:86]=[C:87]([CH2:91][NH2:92])[CH:88]=[CH:89][CH:90]=3)=[N:77]2)C=CC=CC=1>>[CH3:17][C:18]1[C:26]2[C:25](=[O:27])[NH:24][C:23]([C:28]([NH:92][CH2:91][C:87]3[CH:88]=[CH:89][CH:90]=[C:85]([O:84][CH2:83][CH2:82][O:81][C:78]4[N:79]=[CH:80][NH:76][N:77]=4)[CH:86]=3)=[O:30])=[N:22][C:21]=2[S:20][CH:19]=1

Participants

5

Reactant 4

HCID 12516905Ethyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylateHCID 667687691-[2-({3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propyl}oxy)pyridin-4-yl]methanamineHCID 667690991-{3-[(2-([1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy)ethyl)oxy}phenyl]methanamineHCID 135437466Ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylate

Product 1

HCID 1784318725-methyl-4-oxo-N-[(3-{[2-(1H-1,2,4-triazol-3-yloxy)ethyl]oxy}phenyl)methyl]-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide

Procedure

By a method similar to that in Example 22, and using, instead of ethyl 4-oxo-3,4-dihydro-2-quinazolinecarboxylate, ethyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate obtained according to the method described in U.S. Pat. No. 4,054,656 and using, instead of 1-[2-({3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propyl}oxy)pyridin-4-yl]methaneamine, 1-{3-[(2-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy}ethyl)oxy]phenyl}methanamine obtained in Reference Example 32, the title compound was obtained as a white powder (126 mg, 79%).

Workup

  1. customobtained
  2. customobtained in Reference Example 32

Sources & evidence

ORD record
ord-74f644ad3558481486ecefb606a83058
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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