Dimethylformamide → HCID 21882948, compound

HRID 722091Notes

Reaction equation

HRID 722091 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]([OH:21])[C:18]=1[CH2:19][OH:20].[CH2:23](I)[CH3:24].C([O-])([O-])=O.[K+].[K+].CN(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:21][CH2:23][CH3:24])[C:18]=1[CH2:19][OH:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 21882971HCID 21882971, compound

Product 1

HCID 21882948HCID 21882948, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-chloro-9-(5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-9H-purin-2-ylamine (see previous example), EtI (excess), 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: 3.720 min. 1H-NMR (CDCl3) δ 8.27 (s, 1H), 7.90 (s, 1H), 5.40 (s, 2H), 5.11 (s, 2H), 4.85 (d, 2H), 4.50 (t, 1H), 3.95 (q, 2H), 2.51 (s, 3H), 1.45 (t, 3H).

Workup

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

Sources & evidence

ORD record
ord-d96747e81bf54c208a0d0db963f935b2
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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