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3-Nitrophenylboronic Acid → 2-Chloro-7-(3-nitrophenyl)thieno[3,2-d]pyrimidin-4-amine

HRID 1485492
Notes
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Reaction equation

HRID 1485492 reaction equation
Br[C:2]1[C:6]2[N:7]=[C:8]([Cl:12])[N:9]=[C:10]([NH2:11])[C:5]=2[S:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[N+:19]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)([O-:21])=[O:20].CC(C1C=C(C(C)C)C(C2C(P(C(C)(C)C)C(C)(C)C)=CC=CC=2)=C(C(C)C)C=1)C>O1CCOCC1>[Cl:12][C:8]1[N:9]=[C:10]([NH2:11])[C:5]2[S:4][CH:3]=[C:2]([C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:19]([O-:21])=[O:20])[CH:27]=3)[C:6]=2[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 866756507-Bromo-2-chlorothieno[3,2-d]pyrimidin-4-amine

Product 1

HCID 866756532-Chloro-7-(3-nitrophenyl)thieno[3,2-d]pyrimidin-4-amineYield 72.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

7-Bromo-2-chlorothieno[3,2-d]pyrimidin-4-amine (500 mg, 1.90 mmol) was dissolved in dioxane (10 mL) and then 2.0 N sodium carbonate (2.85 mL, 5.70 mmol) and 3-nitrophenylboronic acid (320 mg, 1.90 mmol) were added. After flowing nitrogen to the mixture solution for 10 minutes, Pd2(PPh3)Cl2 (80 mg, 0.11 mmol) and t-Butyl Xphos (73 mg, 0.17 mmol) were added. The reaction mixture solution was stirred at 90° C. for 6 hours, filtered with celite, and washed with ethyl acetate. The aqueous layer was separated from the organic layer and extracted with ethyl acetate. The organic layer was combined, washed with brine, dried with MgSO4, and then concentrated by filtering. Purification by silica gel chromatography (1/4 to 1/3 ethyl acetate/hexane) yielded the target compound (420 mg, 72% yield).

Workup

  1. customfor 10 minutes
  2. filtrationfiltered with celite
  3. washwashed with ethyl acetate
  4. customThe aqueous layer was separated from the organic layer
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated
  9. filtrationby filtering
  10. customPurification by silica gel chromatography (1/4 to 1/3 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-be1025412c1748a2a1981277f43f82c4
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09422307B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes