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Sodium ethoxide → Tert-butyl 4-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)piperazine-1-carboxylate

HRID 1921982
Notes
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Reaction equation

HRID 1921982 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[C:9]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([O:17][CH3:18])[CH:11]=2)=O.Cl.[CH3:34][N:35](N)[C:36]([NH2:38])=[NH:37].[O-]CC.[Na+]>C(O)C>[CH3:18][O:17][C:12]1[CH:11]=[C:10]2[C:15]([CH:16]=[C:7]([C:5]3[CH:4]=[CH:3][N:38]=[C:36]([NH:35][CH3:34])[N:37]=3)[CH:8]=[C:9]2[N:19]2[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:23][CH2:24]2)=[CH:14][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2723922Sodium ethoxide2×HCID 21432264Methyl amino guanidine hydrochlorideHCID 67306919(E)-tert-butyl 4-(3-(3-(dimethylamino)acryloyl)-7-methoxynaphthalen-1-yl)piperazine-1-carboxylate

Product 1

HCID 53257824Tert-butyl 4-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent
2×

Procedure

To a solution of tert-butyl 4-(3-(3-(dimethylamino)acryloyl)-7-methoxynaphthalen-1-yl)piperazine-1-carboxylate 108 (1.5 g) in ethanol (50 ml) was added methyl amino guanidine hydrochloride (0.75 g) and 21% wt sodium ethoxide in ethanol (1 ml). The reaction was stirred at reflux for 2 days, and more sodium ethoxide (0.5 ml) was added to the reaction. The reaction was allowed to reflux overnight. The solvents were concentrated under reduced pressure and the residue was redissolved in ethyl acetate (100 ml) and water (50 ml). The organics were separated, washed with water (1×50 ml), dried over sodium sulfate and concentrated. Column chromatography (pre-packed SiO2, 40% ethyl acetate in hexanes to 75% ethyl acetate in hexanes) gave tert-butyl 4-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)piperazine-1-carboxylate 111 as a light yellow solid. LC/MS (m/z): 450 [M+H].

Workup

  1. temperatureat reflux for 2 days
  2. temperatureto reflux overnight
  3. concentrationThe solvents were concentrated under reduced pressure
  4. dissolutionthe residue was redissolved in ethyl acetate (100 ml)
  5. customThe organics were separated
  6. washwashed with water (1×50 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1e401605b6584671998960ac8640d5e1
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173808B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes