Dimethylformamide → HCID 21882877, compound

HRID 722090Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:14]=[N:15][C:16]([CH3:22])=[C:17](O)[C:18]=1[CH2:19][OH:20].CI.[C:25]([O-:28])([O-])=O.[K+].[K+].[CH3:31]N(C=O)C>CCOC(C)=O>[Cl:1][C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:14]=[N:15][C:16]([CH3:22])=[C:17]([O:28][CH3:25])[C:18]=1[CH2:19][O:20][CH3:31]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 6-chloro-9-(5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-9H-purin-2-ylamine, MeI, K2CO3 (excess) and DMF was heated to 50° C. for 15 min. Work-up (EtOAc), drying (MgSO4), evaporation, and purification by preparative TLC gave the title compound. HPLC Rt: 5.446 min. 1H-NMR (CDCl3) δ 8.35 (s, 1H), 7.70 (s, 1H), 5.35 (s, 2H), 5.25 (s, 2H), 5.15 (s, 2H), 3.80 (s, 3H) 2.59 (s, 3H), 1.970 (s, 3H).

Workup

customdrying
custom(MgSO4), evaporation, and purification by preparative TLC

Sources & evidence

ORD record: ord-ef6ad172085f40abb07d7590254c6b50
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138401B2

Reaction notes

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