Imidazole → 1-(2-Amino-phenyl)-3-[4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-thiourea

HRID 629014Notes

Reaction equation

HRID 629014 reaction equation
N1([C:6]([N:8]2[CH2:12][CH:11]=[N:10]C2)=[S:7])CC=NC1.N1C=CN=C1.[Cl:18][C:19]1[C:24]([S:25][CH3:26])=[C:23]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:22]=[C:21]([C:33]2[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=2)[N:20]=1.[C:40]1(N)[C:41](N)=CC=[CH:44][CH:45]=1>CC#N>[NH2:10][C:11]1[CH:44]=[CH:45][CH:40]=[CH:41][C:12]=1[NH:8][C:6]([NH:39][C:36]1[CH:37]=[CH:38][C:33]([C:21]2[N:20]=[C:19]([Cl:18])[C:24]([S:25][CH3:26])=[C:23]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[N:22]=2)=[CH:34][CH:35]=1)=[S:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 7243O-PhenylenediamineHCID 54042580Bis-(2,5-dihydro-imidazol-1-yl)-methanethioneHCID 86673495HCID 86673495, compound

Product 1

HCID 866735031-(2-Amino-phenyl)-3-[4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-thioureaYield 93.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of bis-(2,5-dihydro-imidazol-1-yl)-methanethione (29.2 mg, 0.164 mmol), imidazole (3.7 mg, 0.05 mmol, 0.5 eq) in CH3CN (5 ml) was stirred at 0° C., then added dropwise to a slurry of 4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenylamine (50 mg, 0.109 mmol.). The resulting mixture was reacted 3.0 hrs at r.t. and then benzene-1,2-diamine (23.6 mg, 0.218 mmol, 2.0 eq) was added thereinto. The reaction resulted in a white solid, which was filtered, collected and evaporated in vacuo to give 49.5 mg of a white compound (68.5%).

Workup

  1. customThe resulting mixture was reacted 3.0 hrs at r.t.
  2. customThe reaction resulted in a white solid, which
  3. filtrationwas filtered
  4. customcollected
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-8d25df26cee84056a586ec8942056db9
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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