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

HRID 606379Notes

Reaction equation

HRID 606379 reaction equation
C(C1C=C2C(=CC=1)N=C(C(OCC)=O)NC2=O)#N.[CH3:19][C:20]1[C:28]2[C:27](=[O:29])[NH:26][C:25]([C:30]([O:32]CC)=O)=[N:24][C:23]=2[S:22][CH:21]=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:42]2[CH:46]=[N:45][C:44]([S:47][CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]3[CH:54]=[C:55]([CH2:59][NH2:60])[CH:56]=[CH:57][CH:58]=3)=[N:43]2)C=CC=CC=1>>[CH3:19][C:20]1[C:28]2[C:27](=[O:29])[NH:26][C:25]([C:30]([NH:60][CH2:59][C:55]3[CH:56]=[CH:57][CH:58]=[C:53]([O:52][CH2:51][CH2:50][CH2:49][CH2:48][S:47][C:44]4[N:45]=[CH:46][NH:42][N:43]=4)[CH:54]=3)=[O:32])=[N:24][C:23]=2[S:22][CH:21]=1

Participants

4

Reactant 3

HCID 12516905Ethyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylateHCID 667682581-{3-[(4-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]thio}butyl)oxy]phenyl}methanamineHCID 136054489Ethyl 6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxylate

Product 1

HCID 1784318715-methyl-4-oxo-N-[(3-{[4-(1H-1,2,4-triazol-3-ylthio)butyl]oxy}phenyl)methyl]-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide

Procedure

By a method similar to that in Example 15, and using, instead of ethyl 6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxylate, ethyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate obtained according to the method described in 034054656 and using, instead of 1-{3-[(3-{(1 (triphenylmethyl)-1H-1,2,4-triazol-3-yl]thiopropyl)oxy}phenyl}methaneamine, 1-{3-[(4-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]thio}butyl)oxy]phenyl}methanamine obtained in Reference Example 11, the title compound was obtained as a pales yellow powder (232 mg, 48%).

Workup

  1. customobtained
  2. customobtained in Reference Example 11

Sources & evidence

ORD record
ord-dc578c74c4f04e81a6c04f211e76afd5
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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