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3-Nitrophenol → 2-Chloro-4-(3-nitrophenoxy)-furo[3,2-d]pyrimidine

HRID 1850022
Notes
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Reaction equation

HRID 1850022 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[N+:12]([C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C(N(C(C)C)CC)(C)C>CO>[Cl:1][C:2]1[N:3]=[C:4]([O:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 111373-NitrophenolHCID 81531DiisopropylethylamineHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidine

Product 1

HCID 866828342-Chloro-4-(3-nitrophenoxy)-furo[3,2-d]pyrimidineYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.4 g (33.9 mmol) of 2,4-dichlorofuro[3,2-d]pyrimidine (see: International Publication Number WO 2008073785 and WO 2008152394) was dissolved in 32 mL of methanol, and 5.7 g (40.6 mmol) of 3-nitrophenol and 12 mL (67.7 mmol) of diisopropylethylamine were added thereto, and stirred for 24 hours at room temperature. Upon the completion of the reaction, the resulting solid was filtered and dried over under a reduced pressure to obtain 6.3 g of the title compound (yield: 64%).

Workup

  1. customUpon the completion of the reaction
  2. filtrationthe resulting solid was filtered
  3. customdried over under a reduced pressure

Sources & evidence

ORD record
ord-1d0351e6f8e94dc4b6cf19dbee77743b
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957065B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes