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

HRID 606381Notes

Reaction equation

HRID 606381 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.Cl.N1C=NC(SCCOC2C=C(CN)C=CN=2)=N1.[C:51]1([C:57]([C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)([C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)[N:58]2[CH:62]=[N:61][C:60]([S:63][CH2:64][CH2:65][O:66][C:67]3[CH:72]=[C:71]([CH2:73][NH2:74])[CH:70]=[CH:69][N:68]=3)=[N:59]2)[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>>[CH3:17][C:18]1[C:26]2[C:25](=[O:27])[NH:24][C:23]([C:28]([NH:74][CH2:73][C:71]3[CH:70]=[CH:69][N:68]=[C:67]([O:66][CH2:65][CH2:64][S:63][C:60]4[N:61]=[CH:62][N:58]([C:57]([C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)([C:75]5[CH:76]=[CH:77][CH:78]=[CH:79][CH:80]=5)[C:81]5[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=5)[N:59]=4)[CH:72]=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 66769079HCID 66769079, compoundHCID 135437466Ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylateHCID 1784791861-(2-{[2-(1H-1,2,4-triazol-3-ylthio)ethyl]oxy}pyridin-4-yl)methanamine hydrochloride

Product 1

HCID 667689495-methyl-4-oxo-N-({2-[(2-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]thio}ethyl)oxy]pyridin-4-yl}methyl)-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide

Procedure

By a method similar to that in Example 19, 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-{[2-(1H-1,2,4-triazol-3-ylthio)ethyl]oxy}pyridin-4-yl)methanamine hydrochloride, 1-{2-[(2-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]thio}ethyl)oxy]pyridin-4-yl}methanamine obtained in Reference Example 20, 5-methyl-4-oxo-N-({2-[(2-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]thio}ethyl)oxy]pyridin-4-yl}methyl)-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide was obtained as a white powder (85 mg, 20%).

Workup

  1. customobtained
  2. customobtained in Reference Example 20

Sources & evidence

ORD record
ord-de195798415e4aa5898186314403738b
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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