Chloride → 8-Methyl-6,7-dihydro-5H-cyclopenta[d][1,2,4]triazolo[-1,5-a]pyrimidine-2-carbaldehyde

HRID 1744959Notes

Reaction equation

CS(C)=O.[Cl-].[CH3:6][C:7]1[N:12]2[N:13]=[C:14]([CH2:16][OH:17])[N:15]=[C:11]2[N:10]=[C:9]2[CH2:18][CH2:19][CH2:20][C:8]=12.C(N(CC)CC)C>ClCCl.O>[CH3:6][C:7]1[N:12]2[N:13]=[C:14]([CH:16]=[O:17])[N:15]=[C:11]2[N:10]=[C:9]2[CH2:18][CH2:19][CH2:20][C:8]=12

Participants

Conditions

Temperature: 23 °C

Procedure

To a round bottomed flask was loaded 0.17 ml of DMSO and l-mi dichloromethane. The mixture was cooled to −50˜−60° C. Then a mixture of 0.1 ml oxallyl chloride and 2 ml dichloromethane was injected in into the flask all at once. The mixture was stirred at the same temperature for another 5 minutes. Then 0.174 grams of (8-Methyl-6,7-dihydro-5H-cyclopenta[d][1,2,4] triazolo [1,5-a]pyrimidin-2-yl)-methanol in 2 ml dichloromethane was added within 2 minutes. The mixture was stirred at −50˜−60° C. for fifteen minutes and 0.7 ml triethylamine was next added. After another five minutes the reaction media was warmed up to 23° C. and a mixture of 20 ml water and 200 ml dichloromethane was added. The organic layer was dried over magnesium sulfate. Filter off the drying agent and concentrate the filtrate yielded 0.153 grams of product (89%). MS: 203.1(M+H). H-NMR(CDCl3): δ 10.24(s, 1H), 3.49(m, 2H), 3.15(m, 2H), 2.67 (s, 3H, CH3), 2.44 (m, 2H, CH2).

Workup

customTo a round bottomed flask was loaded
temperatureThe mixture was cooled to −50˜−60° C
stirringThe mixture was stirred at −50˜−60° C. for fifteen minutes
customAfter another five minutes the reaction media
additionwas added
dry with materialThe organic layer was dried over magnesium sulfate
filtrationFilter off the drying agent
concentrationconcentrate the filtrate

Sources & evidence

ORD record: ord-38559041327e4b8cab7a6c2d01f2cfc0
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07018997B2

Reaction notes

Loading…