Imidazole → HCID 87344994, compound

HRID 628989Notes

Reaction equation

HRID 628989 reaction equation
C1N=CN([C:6]([N:8]2C=[N:11][CH:10]=[CH:9]2)=[S:7])C=1.N1C=CN=C1.[CH2:18]([O:20][C:21]([C:23]1[C:28]([O:29][CH2:30][CH3:31])=[C:27]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[N:26]=[C:25]([C:38]2[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=2)[N:24]=1)=[O:22])[CH3:19].[C:45]1(N)[C:46](N)=CC=[CH:49][CH:50]=1>CC#N>[CH2:18]([O:20][C:21]([C:23]1[C:28]([O:29][CH2:30][CH3:31])=[C:27]([N:32]2[CH2:33][CH2:34][O:35][CH2:36][CH2:37]2)[N:26]=[C:25]([C:38]2[CH:39]=[CH:40][C:41]([NH:44][C:6]([NH:8][C:9]3[CH:49]=[CH:50][CH:45]=[CH:46][C:10]=3[NH2:11])=[S:7])=[CH:42][CH:43]=2)[N:24]=1)=[O:22])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 7243O-PhenylenediamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 67295455HCID 67295455, compound

Product 1

HCID 87344994HCID 87344994, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 1,1-thiocarbonyldiimidazole (216.5 mg, 1.5 eq.), imidazole (164.52 mg, 3 eq.) and CH3CN (10 ml) at 0° C., 2-(4-amino-phenyl)-5-ethoxy-6-morpholin-4-yl-pyrimidine-4-carboxylic acid ethyl ester (300 mg, 1 eq.) dissolved in CH3CN (10 ml) was added dropwise over 10 min. After 10 min, the cooling bath was removed. After 3 h, benzene-1,2-diamine (175.2 mg, 2 eq.) was added and the reaction was heated to 50° C. for 3 h, and then stirred at ambient temperature for 16 h. The solvent was removed by evaporation. The residue was chromatographed to give a thiourea (120 mg, 29%)

Workup

  1. additionwas added dropwise over 10 min
  2. customthe cooling bath was removed
  3. waitAfter 3 h
  4. customThe solvent was removed by evaporation
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-00c537afcefa49d5b78ecbe78e8df756
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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