Ethyl 5-cyanomethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate → 5-(cyanomethyl)-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 606388Notes

Reaction equation

HRID 606388 reaction equation
O=C1C2C(=CC=CC=2)N=C(C(OCC)=O)N1.[C:17]([CH2:19][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)#[N:18].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:78]2[CH:82]=[N:81][C:80]([O:83][CH2:84][CH2:85][O:86][C:87]3[CH:88]=[C:89]([CH2:93][NH2:94])[CH:90]=[CH:91][CH:92]=3)=[N:79]2)C=CC=CC=1>>[C:17]([CH2:19][C:20]1[C:28]2[C:27](=[O:29])[NH:26][C:25]([C:30]([NH:94][CH2:93][C:89]3[CH:90]=[CH:91][CH:92]=[C:87]([O:86][CH2:85][CH2:84][O:83][C:80]4[N:81]=[CH:82][NH:78][N:79]=4)[CH:88]=3)=[O:32])=[N:24][C:23]=2[S:22][CH:21]=1)#[N:18]

Participants

5

Reactant 4

HCID 57708728Ethyl 5-cyanomethyl-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 1785108735-(cyanomethyl)-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-cyanomethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate obtained in Reference Example 61 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 (85.4 mg, 38%).

Workup

  1. customobtained in Reference Example 61
  2. customobtained in Reference Example 32

Sources & evidence

ORD record
ord-2ea840b797574984acd4ed7a3a1527dd
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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