Dichloromethane → HCID 50942862, compound

HRID 1484891Notes

Reaction equation

HRID 1484891 reaction equation
C(Cl)Cl.[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1B(O)O.Cl[C:13]1[N:18]=[C:17]([NH:19][C:20]2[CH:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[NH:22][N:21]=2)[C:16]([Cl:28])=[CH:15][N:14]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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.Cl[Pd]Cl.[Fe+2]>[Cl:28][C:16]1[C:17]([NH:19][C:20]2[CH:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[NH:22][N:21]=2)=[N:18][C:13]([C:5]2[O:4][CH:8]=[CH:7][CH:6]=2)=[N:14][CH:15]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 595867992,5-dichloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine

Product 1

HCID 50942862HCID 50942862, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

The mixture of Pd(dppf)Cl2.CH2Cl2 (100 mg, 0.12 mmol, 0.15 eq), furan-2-ylboronic acid (116 mg, 1.04 mmol, 1.3 eq), 2,5-dichloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (215 mg, 0.80 mmol, 1.0 eq) and aq Na2CO3 (10 mL) in dioxane (20 mL) was heated to 95° C. for 2 h under nitrogen atmosphere. The reaction mixture was cooled to room temperature, and extracted with THF. The combined layers were purified by prep-HPLC to afford compound 5-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(furan-2-yl)pyrimidin-4-amine (Compound 164) (12 mg, 9%). LC-MS (m/z)=302 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 0.73-0.76 (m, 2H), 0.95-0.98 (m, 2H), 1.93-1.97 (m, 1H), 6.53 (s, 1H), 6.68-6.70 (m, 1H), 7.15 (d, J=2.8 Hz, 1H), 7.91 (s, 1H), 8.41 (s, 1H), 9.24 (s, 1H), 12.24 (s, 1 Hz).

Workup

  1. extractionextracted with THF
  2. customThe combined layers were purified by prep-HPLC

Sources & evidence

ORD record
ord-afc3a19e4c644da6b0a41c141844c6ca
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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