Ethyl Glycolate → HCID 23070941, compound

HRID 501377Notes

Reaction equation

HRID 501377 reaction equation
[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10](Cl)=[N:9][C:8]=2[N:7]=[C:6]1[N:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]1)[C:2]#[C:3][CH3:4].[OH:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>C(O)C>[CH2:1]([N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10]([O:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[N:9][C:8]=2[N:7]=[C:6]1[N:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 12184Ethyl GlycolateHCID 23070741t-butyl 4-(7-(2-butynyl)-2-chloro-1-methyl-6-oxo-6,7-dihydro-1H-purin-8-yl]piperazine-1-carboxylate

Product 1

HCID 23070941HCID 23070941, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl [7-(2-butynyl)-1-methyl-6-oxo-8-(piperazin-1-yl)-6,7-dihydro-1H-purin-2-yloxy]acetate trifluoroacetate and [7-(2-butynyl)-1-methyl-6-oxo-8-(piperazin-1-yl)-6,7-dihydro-1H-purin-2-yloxy]acetic acid trifluoroacetate [MS m/e (ESI) 361 (MH+-CF3COOH)] were obtained by treating t-butyl 4-[7-(2-butynyl)-2-chloro-1-methyl-6-oxo-6,7-dihydro-1H-purin-8-yl]piperazine-1-carboxylate using ethyl 2-hydroxyacetate, instead of ethanol, by the same method as used in Example 11. Ethyl [7-(2-butynyl)-1-methyl-6-oxo-8-(piperazin-1-yl)-6,7-dihydro-1H-purin-2-yloxy]acetate trifluoroacetate was purified by chromatography using NH-silica gel. Thus, ethyl [7-(2-butynyl)-1-methyl-6-oxo-8-(piperazin-1-yl)-6,7-dihydro-1H-purin-2-yloxy]acetate [1H-NMR (CDCl3) δ 1.29 (t, J=7.22 Hz, 3H) 1.83 (t, J=2.4 Hz, 3H) 3.02-3.06 (m, 4H) 3.38-3.41 (m, 4H) 3.55 (s, 3H) 4.22 (q, J=7.2 Hz, 2H) 4.90 (q, J=2.4 Hz, 2H) 5.03 (s, 2H); MS m/e (ESI) 389 (MH+)] was obtained from the fraction eluted with ethyl acetate-methanol (20:1)

Workup

  1. customEthyl [7-(2-butynyl)-1-methyl-6-oxo-8-(piperazin-1-yl)-6,7-dihydro-1H-purin-2-yloxy]acetate trifluoroacetate was purified by chromatography

Sources & evidence

ORD record
ord-e17fe35019684361862014565d743e1c
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

Loading…