Sodium Carbonate → HCID 178432617, compound

HRID 2367402Notes

Reaction equation

HRID 2367402 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]3[NH:15][C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:17]([CH3:19])[N:18]=3)[CH2:9]2)[N:5]=[C:4]([NH2:26])[N:3]=1.[F:27][C:28]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:32][C:29]=1[C:30]#[N:31].C([O-])([O-])=O.[Na+].[Na+]>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>[NH2:26][C:4]1[N:3]=[C:2]([C:34]2[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[C:28]([F:27])[CH:35]=2)[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]3[NH:15][C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:17]([CH3:19])[N:18]=3)[CH2:9]2)[N:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 513509512-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileHCID 178432618HCID 178432618, compound

Product 1

HCID 178432617HCID 178432617, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of 4-chloro-6-[2-(4-methyl-5-phenyl-1H-imidazol-2-yl)-4-morpholinyl]-2-pyrimidinamine (1.2 g, 3.24 mmol), 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.199 g, 4.85 mmol), Na2CO3 (0.857 g, 8.09 mmol) and Pd(PPh3)4 (0.374 g, 0.324 mmol) was placed into a microwave vial and heated in Biotage Initiator using initial 150 W to 140° C. for 1 hour. After cooling the reaction, the solvent was removed under reduced pressure, and the crude product was added to a silica gel column and eluted with Hex/EtOAc (1:3) to afford the title compound (1.2 g) as a yellow solid. LC-MS (ES) m/z=456 [M+H]+.

Workup

  1. temperatureheated in Biotage Initiator
  2. customfor 1 hour
  3. temperatureAfter cooling
  4. customthe reaction
  5. customthe solvent was removed under reduced pressure
  6. additionthe crude product was added to a silica gel column
  7. washeluted with Hex/EtOAc (1:3)

Sources & evidence

ORD record
ord-ccdcba70f93a4ed8bcc1128c9e1859d4
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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