tert-butyl N-((3-(aminomethyl)phenyl)methyl)carbamate → 1,1-Dimethylethyl {[3-({[(5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)carbonyl]amino}methyl)phenyl]methyl}carbamate

HRID 606475Notes

Reaction equation

HRID 606475 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.NCC1C=C(C=CC=1)N.[NH2:44][CH2:45][C:46]1[CH:47]=[C:48]([CH2:52][NH:53][C:54](=[O:60])[O:55][C:56]([CH3:59])([CH3:58])[CH3:57])[CH:49]=[CH:50][CH:51]=1>>[CH3:19][C:20]1[C:28]2[C:27](=[O:29])[NH:26][C:25]([C:30]([NH:44][CH2:45][C:46]3[CH:47]=[C:48]([CH2:52][NH:53][C:54](=[O:60])[O:55][C:56]([CH3:58])([CH3:57])[CH3:59])[CH:49]=[CH:50][CH:51]=3)=[O:32])=[N:24][C:23]=2[S:22][CH:21]=1

Participants

5

Reactant 4

HCID 2756043tert-butyl N-((3-(aminomethyl)phenyl)methyl)carbamateHCID 46288313-AminobenzylamineHCID 12516905Ethyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylateHCID 136054489Ethyl 6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxylate

Product 1

HCID 577087471,1-Dimethylethyl {[3-({[(5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)carbonyl]amino}methyl)phenyl]methyl}carbamate

Procedure

By a method similar to that in Reference Example 45, 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 U.S. Pat. No. 4,054,656 and using, instead of 3-(aminomethyl)aniline, 1,1-dimethylethyl {[3-(aminomethyl)phenyl]methyl}carbamate, the title compound was obtained as a white powder (2.11 g, 82%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-f0583ab164844dfabc236c9680b3d51b
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

Loading…