Methylamine → HCID 131726909, compound

HRID 130307Notes

Reaction equation

[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][CH:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:25]1[CH:29]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:27]=[N:26]1)=[N:14][C:15]=2[NH:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.[CH3:35][NH2:36]>O>[CH2:33]([O:32][C:30]([C:28]1[N:27]=[N:26][N:25]([C:13]2[N:12]=[C:11]3[C:16]([N:17]=[CH:18][N:10]3[CH:3]3[C@H:2]([OH:1])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4]3)=[C:15]([NH:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[N:14]=2)[CH:29]=1)=[O:31])[CH3:34].[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:25]1[CH:29]=[C:28]([C:30]([NH:36][CH3:35])=[O:32])[N:27]=[N:26]1)=[N:14][C:15]=2[NH:19][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

Conditions

Temperature: 50 °C

Procedure

70 mg of the ethyl 1-{9-[(4S,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}-1,2,3-triazole-4-carboxylate prepared in Example 4A was dissolved in 5 mL of 40% methylamine in water in a sealed tube. The mixture was stirred at 50° C. for 2 hours. A white precipitate formed and was collected by filtration. The collected filtrate was washed with water and ethyl ether to provide the product, (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}(1,2,3-triazol-4-yl))-N-methylcarboxamide ethyl 1-{9-[(4S,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}-1,2,3-triazole-4-carboxylate.

Workup

customA white precipitate formed
filtrationwas collected by filtration
washThe collected filtrate was washed with water and ethyl ether

Sources & evidence

ORD record: ord-84490e101ff1474aa150bd956f8f2c9d
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381714B2

Reaction notes

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