Triphenylphosphine → N-(4-chloro-3-(4-methylpent-3-en-2-yloxy)phenyl)pyrimidin-2-amine

HRID 1474026Notes

Reaction equation

HRID 1474026 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[OH:15].[CH3:16][C:17]([CH3:22])=[CH:18][CH:19](O)[CH3:20].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)=[CH:4][C:3]=1[O:15][CH:19]([CH:18]=[C:17]([CH3:22])[CH3:16])[CH3:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1381904-Methylpent-3-en-2-olHCID 5462977Diethyl azodicarboxylateHCID 594749452-Chloro-5-(pyrimidin-2-ylamino)phenol

Product 1

HCID 86645050N-(4-chloro-3-(4-methylpent-3-en-2-yloxy)phenyl)pyrimidin-2-amineYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flask was added 2-chloro-5-(pyrimidin-2-ylamino)phenol (50 mg, 0.23 mmol), 4-methylpent-3-en-2-ol (23 mg, 0.23 mmol), Ph3P (59 mg, 0.23 mmol) and THF (0.08 mL). The reaction vessel was lowered into a sonication bath and sonicated for several minutes giving a clear and highly viscous solution. While sonication, DEAD (0.044 mL, 0.23 mmol) was added. After 1 h, the reaction mixture was concentrated in vacuo and the crude product was purified by flash chromatography on silica gel (hexane:EtOAc 7/3) to give the product in 17% yield (12 mg).

Workup

  1. customThe reaction vessel was lowered into a sonication bath
  2. customsonicated for several minutes
  3. customgiving a clear and highly viscous solution
  4. additionwas added
  5. concentrationthe reaction mixture was concentrated in vacuo
  6. customthe crude product was purified by flash chromatography on silica gel (hexane:EtOAc 7/3)
  7. customto give the product in 17% yield (12 mg)

Sources & evidence

ORD record
ord-386f609eef8240f0abaae02365669c25
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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