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Sodium Carbonate → 4-Chloro-5-cyclopropyl-2,6-dimethoxy-pyrimidine

HRID 426251
Notes
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Reaction equation

HRID 426251 reaction equation
Br[C:2]1[C:3]([Cl:12])=[N:4][C:5]([O:10][CH3:11])=[N:6][C:7]=1[O:8][CH3:9].[CH:13]1(B(O)O)[CH2:15][CH2:14]1.ClCl.C([O-])([O-])=O.[Na+].[Na+]>[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C(OCC)(=O)C.COCCOC>[Cl:12][C:3]1[C:2]([CH:13]2[CH2:15][CH2:14]2)=[C:7]([O:8][CH3:9])[N:6]=[C:5]([O:10][CH3:11])[N:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 24526ChlorineHCID 2760897Cyclopropylboronic acidHCID 122261955-Bromo-4-chloro-2,6-dimethoxypyrimidine

Product 1

HCID 591847574-Chloro-5-cyclopropyl-2,6-dimethoxy-pyrimidineYield 65.2%

Reagents, catalysts & solvents 4

HCID 23938
Palladium
Catalyst
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst
HCID 80711,2-DimethoxyethaneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

In a 5 mL microwave reaction tube, 5-bromo-4-chloro-2,6-dimethoxy-pyrimidine (116 mg, 0.457 mmol), cyclopropyl boronic acid (47 mg, 0.549 mmol, 1.2 eq.) and Pd(dppf(Cl2 (38 mg, 0.1 eq.) was charged with DME (2.5 mL) and 2M Na2CO3 aqueous solution (0.91 mL, 4 eq.). The reaction was heated at 130° C. in the microwave reactor for 30 minutes. Ethyl acetate was added, followed by washing with brine. The organic layer was concentrated down and purified (silica gel, 0-50% EtOAC/hexane) to give white solid (64 mg, 65%). LC-MS shows 215.1 (M+1). 1H NMR (300 MHz, CDCl3): δ 3.98 (dd, 6H), 1.62 (m, 1H), 0.99 (m, 2H), 0.78 (m, 2H).

Workup

  1. washby washing with brine
  2. concentrationThe organic layer was concentrated down
  3. custompurified (silica gel, 0-50% EtOAC/hexane)

Sources & evidence

ORD record
ord-c5ba8d2c36214879b6a22c42ec5498a5
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106064B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes