Phosphorus oxychloride → 2-Azidomethyl-7-chloro-5-methyl[1.2.4]triazolo[1,5-a]pyrimidine

HRID 1755923Notes

Reaction equation

[N:1]([CH2:4][C:5]1[N:15]=[C:8]2[N:9]=[C:10]([CH3:14])[CH:11]=[C:12](O)[N:7]2[N:6]=1)=[N+:2]=[N-:3].P(Cl)(Cl)([Cl:18])=O>N1C=CC=CC=1>[N:1]([CH2:4][C:5]1[N:15]=[C:8]2[N:9]=[C:10]([CH3:14])[CH:11]=[C:12]([Cl:18])[N:7]2[N:6]=1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 50 °C

Procedure

2-Azidomethyl-5-methyl[1.2.4]-triazolo[1,5-a]-pyrimidin-7-ol (3.1 g) are suspended in 20 ml of freshly distilled phosphorus oxychloride and 1.1 ml of pyridine and stirred at 50° C. for 4.5 hours. The phosphorus oxychloride is evaporated in a vacuum and the residue is taken up in 40 ml of ethyl acetate and 40 ml of water. The resulting suspension is stirred in an ice bath for 45 minutes. The product is filtered off under suction and dried in a vacuum at 40° C. There are obtained 2.1 g of 2-azidomethyl-7-chloro-5-methyl[1.2.4]triazolo[1,5-a]pyrimidine as white crystals of melting point 130°-132° C.

Workup

customThe phosphorus oxychloride is evaporated in a vacuum
stirringThe resulting suspension is stirred in an ice bath for 45 minutes
filtrationThe product is filtered off under suction
customdried in a vacuum at 40° C

Sources & evidence

ORD record: ord-84354c9723d940fb94a4b54f18566b28
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05438052

Reaction notes

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