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Methanol → 8-[1-Cyano-4-(1,3-dimethyl-2,4,6-trioxo-tetrahydro-pyrimidin-5-ylidene)-but-2-enylidene]-10,10-dimethyl-8,10-dihydro-pyrido[1,2-a]indol-2-ylmethyl-ammonium iodide

HRID 76820
Notes
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Reaction equation

HRID 76820 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]1[CH:18]=[CH:19][C:20](=[C:22]([C:37]#[N:38])[CH:23]=[CH:24][CH:25]=[C:26]3[C:31](=[O:32])[N:30]([CH3:33])[C:29](=[O:34])[N:28]([CH3:35])[C:27]3=[O:36])[CH:21]=[C:13]1[C:12]2([CH3:40])[CH3:39])(C)(C)C.[I:42][Si](C)(C)C.CO>C(#N)C>[I-:42].[C:37]([C:22](=[C:20]1[CH:19]=[CH:18][N:14]2[C:15]3[C:11]([C:12]([CH3:40])([CH3:39])[C:13]2=[CH:21]1)=[CH:10][C:9]([CH2:8][NH3+:7])=[CH:17][CH:16]=3)[CH:23]=[CH:24][CH:25]=[C:26]1[C:27](=[O:36])[N:28]([CH3:35])[C:29](=[O:34])[N:30]([CH3:33])[C:31]1=[O:32])#[N:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodide2×HCID 76688216{8-[1-Cyano-4-(1,3-dimethyl-2,4,6-trioxo-tetrahydro-pyrimidin-5-ylidene)-but-2-enylidene]-10,10-dimethyl-8,10-dihydro-pyrido[1,2-a]indol-2-ylmethyl}-carbamic acid tert-butyl ester

Product 1

HCID 866512048-[1-Cyano-4-(1,3-dimethyl-2,4,6-trioxo-tetrahydro-pyrimidin-5-ylidene)-but-2-enylidene]-10,10-dimethyl-8,10-dihydro-pyrido[1,2-a]indol-2-ylmethyl-ammonium iodide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

{8-[1-Cyano-4-(1,3-dimethyl-2,4,6-trioxo-tetrahydro-pyrimidin-5-ylidene)-but-2-enylidene]-10,10-dimethyl-8,10-dihydro-pyrido[1,2-a]indol-2-ylmethyl}-carbamic acid tert-butyl ester (20 g, 0.04 mol; Sigma-Aldrich) from previous step was placed in one-necked round bottom 1 L flask equipped with magnetic stir bar and dissolved in 150 mL of acetonitrile. The flask was closed with rubber septa and flashed with dry nitrogen. 10 g of iodotrimethylsilane were added to the flask with use of syringe, and reaction mixture was stirred at room temperature for 30 min. During addition of iodotrimethylsilane the color of the flask changed from deep blue to deep orange. 25 mL of methanol were added to the reaction mixture and its color become deep blue again. The volume of reaction mixture was reduced in about half using rotary evaporator. During this operation most of the methanol was removed from the reaction mixture and the product, which is insoluble in acetonitrile, precipitates. The product was filtered, washed with acetonitrile, dried and transferred to a 500-mL conical flask equipped with magnetic stirrer. 200 mL of dichloromethane were added to the flask, and flask content was stirred with mild heating (very gentle DCM boiling) for 10 min. The mixture was filtered when still hot, the dye was washed with DCM and dried. The yield was 10 g (50% of theory based on two steps).

Workup

  1. customequipped with magnetic stir bar
  2. customThe flask was closed with rubber septa
  3. customreaction mixture
  4. customThe volume of reaction mixture
  5. customwas reduced in about half using rotary evaporator
  6. customDuring this operation most of the methanol was removed from the reaction mixture
  7. customprecipitates
  8. filtrationThe product was filtered
  9. washwashed with acetonitrile
  10. customdried
  11. customtransferred to a 500-mL conical flask
  12. customequipped with magnetic stirrer
  13. addition200 mL of dichloromethane were added to the flask, and flask content
  14. stirringwas stirred
  15. temperaturewith mild heating (very gentle DCM boiling) for 10 min
  16. filtrationThe mixture was filtered when still hot
  17. washthe dye was washed with DCM
  18. customdried

Sources & evidence

ORD record
ord-94635319d7404dd2a52af5a0aafb6411
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835632B2

Reaction notes

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