Diisopropylethylamine → 2-Allyl-5-(4-cyanophenyl)-7-methyl-3-oxo-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylic acid methyl ester

HRID 2362296Notes

Reaction equation

HRID 2362296 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:7]=[C:8](OC)[NH:9][C:10]=1[CH3:11])=[O:4].Cl[C:23](OC1C=CC([N+]([O-])=O)=CC=1)=[O:24].Cl.[CH2:36]([NH:39][NH2:40])[CH:37]=[CH2:38].CCN(C(C)C)C(C)C>C(Cl)Cl.N1C=CC=CC=1.CC#N>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:14]2[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=2)[N:7]2[C:23](=[O:24])[N:39]([CH2:36][CH:37]=[CH2:38])[N:40]=[C:8]2[NH:9][C:10]=1[CH3:11])=[O:4]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 171127Allylhydrazine hydrochlorideHCID 674375874-(4-Cyanophenyl)-2-methoxy-6-methyl-1,4-dihydropyrimidine-5-carboxylic acid methyl ester

Product 1

HCID 1363595122-Allyl-5-(4-cyanophenyl)-7-methyl-3-oxo-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylic acid methyl esterYield 56.9%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Intermediate 4 (1.42 g, 5 mmol) was dissolved in a mixture of DCM (10 mL) and pyridine (10 mL) and cooled using an ice bath. A solution of 4-nitrophenyl chloroformate (0.955 mg, 4.75 mmol) in DCM (10 mL) was added dropwise, and the resulting solution was stirred at 0° C. for 1.5 hours, and then a solution of allyl hydrazine hydrochloride (1.0 g, 5.5 mmol) and DIPEA (3.75 mL, 22 mmol) in CH3CN (10 mL) was added in one portion. The resulting mixture was allowed to warm to RT, stirred for 4 hours, and then partitioned between EtOAc and water. The organic layer was separated, washed with water, followed by brine, then dried (Na2SO4) and evaporated in vacuo to yield the title compound as a yellow oil (0.95 g).

Workup

  1. temperaturecooled
  2. temperatureto warm to RT
  3. stirringstirred for 4 hours
  4. custompartitioned between EtOAc and water
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-80cbf3ef0c9c402c8333f7f328b046c9
Source dataset
uspto-grants-2014_04
Patent number
US08691826B2

Reaction notes

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