Water → HCID 66826985, compound

HRID 1468616Notes

Reaction equation

CC1C=CC(S([O:11][CH2:12][CH2:13][N:14]2[CH:18]3[N:19]=[C:20]4[C:25]([N:17]3[N:16]([CH2:32][CH:33]3[CH2:35][CH2:34]3)[C:15]2=[O:36])=[C:24]([C:26]2[O:27][CH:28]=[CH:29][CH:30]=2)[N:23]=[CH:22][N:21]4[NH2:31])(=O)=O)=CC=1.[F:37][C:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[NH2:31][N:21]1[C:20]2[C:25]([N:17]3[N:16]([CH2:32][CH:33]4[CH2:34][CH2:35]4)[C:15](=[O:36])[N:14]([CH2:13][CH2:12][O:11][C:41]4[CH:42]=[CH:43][C:38]([F:37])=[CH:39][CH:40]=4)[CH:18]3[N:19]=2)=[C:24]([C:26]2[O:27][CH:28]=[CH:29][CH:30]=2)[N:23]=[CH:22]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-[5-amino-1-(cyclopropylmethyl)-8-(2-furyl)-2-oxo-[1,2,4]triazolo[5,1-f]purin-3-yl]ethyl 4-methylbenzenesulfonate obtained in step 7 of C1 (0.045 g, 0.088 mmol), 4-fluorophenol (0.018 g, 0.176 mmol) and K2CO3 (0.036 g, 0.22 mmol) were taken in DMF (2 ml) and stirred at 80° C. for 16 hours. To the reaction mixture water (25 ml) was added and extracted with ethyl acetate (3×20 ml). The crude product was purified by column chromatography to 5-amino-1-(cyclopropylmethyl)-3-[2-(4-fluorophenoxy)ethyl]-8-(2-furyl)-[1,2,4]triazolo[5,1-f]purin-2-one (8 mg, 20%) as an off white solid

Workup

extractionextracted with ethyl acetate (3×20 ml)
customThe crude product was purified by column chromatography to 5-amino-1-(cyclopropylmethyl)-3-[2-(4-fluorophenoxy)ethyl]-8-(2-furyl)-[1,2,4]triazolo[5,1-f]purin-2-one (8 mg, 20%) as an off white solid

Sources & evidence

ORD record: ord-19424147d67a4ccfb22e28a143dbf638
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006177B2

Reaction notes

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