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Tetrahydrofuran → N-(3-methyl-benzylidene)-N'-[6-morpholin-4-yl-2-(2-morpholin-4-yl-ethyl)-pyrimidin-4-yl]-hydrazine

HRID 252981
Notes
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Reaction equation

HRID 252981 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH:5]=[N:6][NH:7][C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:11]=[C:10]([CH2:20]COS(C)(=O)=O)[N:9]=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.O1CCC[CH2:37]1>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH:5]=[N:6][NH:7][C:8]1[CH:13]=[C:12]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[N:11]=[C:10]([CH2:20][CH2:37][N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 76837803methanesulfonic acid 2-{4-[N'-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethyl ester

Product 1

HCID 66841256N-(3-methyl-benzylidene)-N'-[6-morpholin-4-yl-2-(2-morpholin-4-yl-ethyl)-pyrimidin-4-yl]-hydrazine

Conditions

Temperature
80 °C

Procedure

Compound 95, methanesulfonic acid 2-{4-[N′-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethyl ester (104 mg., 0.25 mmol) was dissolved in tetrahydrofuran (4 mL). To the reaction mixture was added morpholine (43 mg., 0.5 mmol) and the vessel was sealed and heated at 80° C. for sixteen hours. The solvent was removed under reduced pressure and the crude oil was purified by column chromatography to give Compound 94, N-(3-methyl-benzylidene)-N′-[6-morpholin-4-yl-2-(2-morpholin-4-yl-ethyl)-pyrimidin-4-yl]-hydrazine (52 mg., 0.13 mmol).

Workup

  1. customthe vessel was sealed
  2. customThe solvent was removed under reduced pressure
  3. customthe crude oil was purified by column chromatography

Sources & evidence

ORD record
ord-5f97ff75891c4be2be54874a7b2662d8
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07872005B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes