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Sodium Carbonate → 5-(4-Decyl-2,3-difluorophenyl)-2-(6-hexyloxypyridin-3-yl)pyrimidine

HRID 376776
Notes
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Reaction equation

HRID 376776 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[N:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:13]=2)=[N:6][CH:7]=1.[CH2:21]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[C:33]([F:40])[C:32]=1[F:41])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:21]([C:31]1[CH:36]=[CH:35][C:34]([C:2]2[CH:3]=[N:4][C:5]([C:8]3[CH:9]=[N:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:13]=3)=[N:6][CH:7]=2)=[C:33]([F:40])[C:32]=1[F:41])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 109697305-Bromo2-(6-hexyloxypyridin-3-yl)pyrimidineHCID 19359100(4-Decyl-2,3-difluorophenyl)boronic acid

Product 1

HCID 193591125-(4-Decyl-2,3-difluorophenyl)-2-(6-hexyloxypyridin-3-yl)pyrimidineYield 39.2%

Reagents, catalysts & solvents 4

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Procedure

The reaction of 2 mmol of 5-bromo-2-(6-hexyloxypyridin-3-yl)pyrimidine, 2 mmol of 4-decyl-2,3-difluorophenylboronic acid, 4 mmol of sodium carbonate and 0.02 mmol of tetrakis(triphenylphosphine)palladium(0) in 8 ml of toluene, 3 ml of ethanol and 3 ml of water is carried out analogously to the procedure indicated for Example 1a). The crude product is separated off by column chromatography on silica gel 60 using ethyl acetate as eluent and is recrystallized from acetonitrile, giving 0.4 g (39%) of colorless crystals, X 96 SA 127 I.

Workup

  1. customThe crude product is separated off by column chromatography on silica gel 60 using ethyl acetate as eluent
  2. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-cbf17ac38a74456aad65cfc01f980d50
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06022492

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes