Ethyl isocyanate → (S)-1-ethyl-3-(3-methyl-4-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea

HRID 1626622Notes

Reaction equation

HRID 1626622 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[C:9]1[N:10]=[C:11]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]2[CH3:26])[C:12]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C:13]=2[N:14]=1)[NH2:5].[CH2:27]([N:29]=[C:30]=[O:31])[CH3:28]>>[CH2:27]([NH:29][C:30]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([C:9]2[N:10]=[C:11]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]3[CH3:26])[C:12]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C:13]=3[N:14]=2)=[C:2]([CH3:1])[CH:3]=1)=[O:31])[CH3:28]

Participants

3

Reactant 2

HCID 8022Ethyl isocyanateHCID 66688545(S)-3-methyl-4-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)aniline

Product 1

HCID 66679215(S)-1-ethyl-3-(3-methyl-4-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)ureaYield 20%

Procedure

Method as example 85 using (S)-3-methyl-4-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)aniline and ethyl isocyanate as starting materials. The solvent was removed in vacuo and purified by prep HPLC (high pH) yielding the title compound (11.8 mg, 0.027 mmol, 20%).

Workup

  1. customThe solvent was removed in vacuo
  2. custompurified by prep HPLC (high pH)

Sources & evidence

ORD record
ord-9ce87b4325ff4daf8910d96f4cff29ae
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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