1,1'-Carbonyldiimidazole → 5-Benzyl-2-(3-cyclopropyl-[1,2,4]oxadiazol-5-ylmethylsulfanyl)-pyrimidin-4-ylamine

HRID 722081Notes

Reaction equation

HRID 722081 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][N:5]=[C:4]([S:15][CH2:16][C:17]([OH:19])=O)[N:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O[NH:33][C:34]([CH:36]1[CH2:38][CH2:37]1)=[NH:35]>CN(C=O)C>[CH2:8]([C:7]1[C:2]([NH2:1])=[N:3][C:4]([S:15][CH2:16][C:17]2[O:19][N:35]=[C:34]([CH:36]3[CH2:38][CH2:37]3)[N:33]=2)=[N:5][CH:6]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 21883178(4-Amino-5-benzyl-pyrimidin-2-ylsulfanyl)-acetic acidHCID 178513214HCID 178513214, compound

Product 1

HCID 98810425-Benzyl-2-(3-cyclopropyl-[1,2,4]oxadiazol-5-ylmethylsulfanyl)-pyrimidin-4-ylamineYield 9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4-amino-5-benzyl-pyrimidin-2-ylsulfanyl)-acetic acid (0.35 mg, 1.27 mmol) as prepared according to the method described in example 22, and 1,1′-carbonyl-diimidazole (0.31 g, 1.91 mmol) in DMF (8 ml) was stirred at room temperature for 3 h and subsequently N-hydroxy-cyclopropanecarboxamidine (0.19 g, 1.91 mmol) was added. The reaction mixture was stirred at 80° C. for 20 h and evaporated. Acetic acid (10 ml) was added and the stirred mixture was heated under reflux conditions for 2 h. Aqueous work-up, column chromatography on silica gel (ethyl acetate/hexane 3:2) and crystallization from ethyl acetate/hexane yielded the title compound (36 mg, 9%) as an off-white solid, m.p. 94° C. and MS: m/e=340.3 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred at 80° C. for 20 h
  2. customevaporated
  3. additionAcetic acid (10 ml) was added
  4. temperaturethe stirred mixture was heated under reflux conditions for 2 h
  5. customAqueous work-up, column chromatography on silica gel (ethyl acetate/hexane 3:2) and crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c8a2dffda92146cdb0d4e4bf84002145
Source dataset
uspto-grants-2006_11
Patent number
US07138404B2

Reaction notes

Loading…