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Dimethylformamide dimethyl acetal → Ethyl 4-(4-cyanophenyl)-2-{[2-(2-quinolylamino)ethyl]amino}pyrimidine-5-carboxylate

HRID 31745
Notes
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Reaction equation

HRID 31745 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2].CN(C(OC)OC)C.[N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[NH:35][CH2:36][CH2:37][NH:38][C:39]1[N:44]=C(C2C=CC(C(N)=O)=CC=2)C=[CH:41][N:40]=1.[O-]CC.[Na+]>C(O)C.C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:41][N:40]=[C:39]([NH:38][CH2:37][CH2:36][NH:35][C:26]3[CH:27]=[CH:28][C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:25]=3)[N:44]=2)=[CH:5][CH:4]=1)#[N:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 78373Dimethylformamide dimethyl acetalHCID 2723922Sodium ethoxideHCID 2757969Ethyl 3-(4-Cyanophenyl)-3-oxopropionateHCID 221701114-(2-{[2-(2-Quinolylamino)ethyl]amino}pyrimidin-4-yl)benzamide

Product 1

HCID 22170113Ethyl 4-(4-cyanophenyl)-2-{[2-(2-quinolylamino)ethyl]amino}pyrimidine-5-carboxylate

Reagents, catalysts & solvents

2
HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 3-(4-cyanophenyl)3-oxopropanoate (64 mg, 0.3 mmol) was heated with DMFDMA (50 μl) and dry THF (1 ml) at 70° C. for 3 hours. The cooled mixture was then added to a suspension of amino[2-(2-quinolylamino)ethyl]carboxamidinium 4-methylbenzenesulfonate (prepared according to Example 12), (120 mg, 0.3 mmol) in ethanol (2 ml) containing 0.35 mmol of sodium ethoxide. The reaction was then heated at 80° C. overnight and then concentrated in vacuo. The residue was taken up in dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic layer was concentrated in vacuo. The residue was taken up in acetonitrile. Addition of water gave a precipitate which was filtered off and dried to give the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate
  3. concentrationThe organic layer was concentrated in vacuo
  4. additionAddition of water
  5. customgave a precipitate which
  6. filtrationwas filtered off
  7. customdried

Sources & evidence

ORD record
ord-b7a0db0625e64582a993f489951dfd43
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425557B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes