2-Nitrophenol → HCID 17986374, compound

HRID 970437Notes

Reaction equation

HRID 970437 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][CH2:12][OH:13])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1O)([O-:16])=[O:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][CH2:12][O:13][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N+:14]([O-:16])=[O:15])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 69472-NitrophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 17986388HCID 17986388, compound

Product 1

HCID 17986374HCID 17986374, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.06 g (4.0 mmol) of 3-(5-bromo-2-chloro-pyrimidin-4-ylamino)-propan-1-ol, 0.65 g (4.8 mmol) of 2-nitro-phenol and 1.25 g (4.8 mmol) of triphenylphosphine in 30 ml of THF is mixed under argon at 0° C. with 0.8 ml of DEAD. The reaction mixture is heated to room temperature while being stirred. After 20 hours, the batch is spun in, and the residue is purified by chromatography (hexane/ethyl acetate 3:1, Flashmaster II). 1.15 g (3.0 mmol, corresponding to 74% of theory) of the product is obtained.

Workup

  1. customis purified by chromatography (hexane/ethyl acetate 3:1, Flashmaster II)
  2. custom1.15 g (3.0 mmol, corresponding to 74% of theory) of the product is obtained

Sources & evidence

ORD record
ord-74e3cf64895b405d9269a16ef9793b7a
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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