Triphenylphosphine → 2,5,6-Triamino-4-[4-(2,2,2-trifluoro-acetylamino-methyl)-benzyloxy]-pyrimidine

HRID 1695097Notes

Reaction equation

HRID 1695097 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])=[CH:12][CH:11]=2)[C:5]([N:24]=O)=[C:4]([NH2:26])[N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC1C=CC=CC=1C>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][NH:17][C:18](=[O:23])[C:19]([F:22])([F:20])[F:21])=[CH:14][CH:15]=2)[C:5]([NH2:24])=[C:4]([NH2:26])[N:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 866156112,6-Diamino-5-nitroso-4-[4-(2,2,2-trifluoro-acetamidomethyl)-benzyloxy]-pyrimidine

Product 1

HCID 866156132,5,6-Triamino-4-[4-(2,2,2-trifluoro-acetylamino-methyl)-benzyloxy]-pyrimidine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2,6-Diamino-5-nitroso-4-[4-(2,2,2-trifluoro-acetylamino-methyl)-benzyloxy]-pyrimidine (1.22 g, 3.3 mmol) and triphenylphosphine (1.89 g, 7 mmol) in 20 mL o-xylene are heated to reflux for 1 h. After cooling to room temperature the solvent is removed in vacuo and the remaining residue redissolved in methanol. The residue is adsorbed on SiO2 and purified by flash column chromatography (CH2Cl2/methanol 95:5 to 5:1) to yield the title compound.

Workup

  1. temperatureto reflux for 1 h
  2. customis removed in vacuo
  3. dissolutionthe remaining residue redissolved in methanol
  4. custompurified by flash column chromatography (CH2Cl2/methanol 95:5 to 5:1)

Sources & evidence

ORD record
ord-df96de5705b944fdb766154e7aea13f9
Source dataset
uspto-grants-2012_04
Patent number
US08163479B2

Reaction notes

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