Triphenylphosphine → HCID 11494843, compound

HRID 216186Notes

Reaction equation

HRID 216186 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[C:16]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:15]=[C:14]([O:29][CH3:30])[N:13]=2)=[CH:8][C:4]=1[CH:5]=[N:6]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClN1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[C:16]([NH:18][CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[N:15]=[C:14]([O:29][CH3:30])[N:13]=2)=[CH:8][C:4]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 73033762HCID 73033762, compound

Product 1

HCID 11494843HCID 11494843, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxy-5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzaldehyde oxime [0.49 g, 1.2 mmol, Example 26(c)], and triphenylphosphine (0.63 g, 2.4 mmol) in DCM (20 mL) is added N-chloro-succinimide (0.32 g, 2.4 mmol) at 10° C. After 2 hours at 20° C., the mixture is concentrated, and subjected to chromatography on silica gel eluting with 5% to 10% MeOH in DCM to afford 2-methoxy-5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzonitrile [0.4 g, 85%, Example 55]. LCMS: RT=2.75 minutes, MS: 391 (M+H).

Workup

  1. concentrationthe mixture is concentrated

Sources & evidence

ORD record
ord-18f321e1524542baaf68df4bc1034e68
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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