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methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate → (7S)-2-chloro-8-isopropyl-7-ethyl-5,7-dihydropteridin-6-one

HRID 2364765
Notes
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Reaction equation

HRID 2364765 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH:16]([CH3:18])[CH3:17])[C@@H:9]([CH2:14][CH3:15])[C:10](OC)=[O:11])[C:5]([N+:19]([O-])=O)=[CH:4][N:3]=1>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:19][C:10](=[O:11])[C@H:9]([CH2:14][CH3:15])[N:8]([CH:16]([CH3:18])[CH3:17])[C:6]=2[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 86668260methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate

Product 1

HCID 86668261(7S)-2-chloro-8-isopropyl-7-ethyl-5,7-dihydropteridin-6-oneYield 101.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

Methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-isopropyl-amino]butanoate 43b (8.74 g, 27.7 mmol) was dissolved in 100 mL of acetic acid followed by the addition of iron powder (6.20 g, 0.11 mol). The reaction mixture was heated to 65° C., stirred for 4 hours and filtered. The filter cake was washed with dichloromethane (100 mL). The filtrate was concentrated under reduced pressure, then added with 100 mL of water and filtered. The filter cake was dried by heating to obtain the crude compound (7S)-2-chloro-8-isopropyl-7-ethyl-5,7-dihydropteridin-6-one 43c (7.17 g) as a gray solid, which was used in the next step without further furification.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with dichloromethane (100 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionadded with 100 mL of water
  5. filtrationfiltered
  6. customThe filter cake was dried
  7. temperatureby heating

Sources & evidence

ORD record
ord-1cfa8b8742dd4a249103e1d97f09e2c4
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691822B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes