Isopropanol → HCID 60204687, compound

HRID 2267474Notes

Reaction equation

HRID 2267474 reaction equation
[Br:1][C:2]1[C:3]([C:9]2[S:10][C:11]([CH2:14][N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:13]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:21][CH2:22][CH2:23][N:24]1[CH2:28][CH2:27][NH:26][C:25]1=[O:29].C(O)(C)C>ClCCl>[Br:1][C:2]1[C:3]([C:9]2[S:10][C:11]([CH2:14][N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:13]=2)=[N:4][C:5]([NH:21][CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][NH:26][C:25]2=[O:29])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 80480N-(2-Aminoethyl)ethyleneureaHCID 60204686HCID 60204686, compound

Product 1

HCID 60204687HCID 60204687, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
170 °C

Procedure

5-Bromo-2-chloro-4-(5-(piperidin-1-ylmethyl)thiophen-2-yl)pyrimidine (0.3 g, 0.8 mmol), 1-(2-aminoethyl)imidazolidin-2-one (0.123 g, 0.96 mmol) and isopropyl alcohol were all placed in a microwave tube. The tube was capped and heated to 170° C. in a Personal Chemistry microwave for 10 min. The reaction then diluted with dichloromethane washed with water, saturated sodium bicarbonate, water and brine. The organic layer was dried with sodium sulfate and purified by flash chromatography using a gradient of 2 to 12% methanol in dichloromethane to give a light yellow solid (0.23 g). MS (M+H)+ 465/476.

Workup

  1. customall placed in a microwave tube
  2. customThe tube was capped
  3. customThe reaction
  4. washwashed with water, saturated sodium bicarbonate, water and brine
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-026ea3c91e734caa82253445bcb4194d
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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