Triphenylphosphine → HCID 54698317, compound

HRID 1012985Notes

Reaction equation

HRID 1012985 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:15]([OH:16])=[C:14]([OH:17])[N:13]=[C:12]([C:18]([NH:21][CH2:22][CH2:23][CH2:24]O)([CH3:20])[CH3:19])[N:11]=2)=[O:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:18]([CH3:20])([CH3:19])[NH:21][CH2:22][CH2:23][CH2:24][N:13]3[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178457324HCID 178457324, compound

Product 1

HCID 54698317HCID 54698317, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude N-(4-fluorobenzyl)-5,6-dihydroxy-2-{1-[(3-hydroxypropyl)amino]-1-methylethyl}pyrimidine-4-carboxamide prepared as described in Step 1 was dissolved in THF, and treated with triphenylphosphine (1.5 eq.) and DEAD (1.5 eq.). The mixture was stirred under nitrogen, after 14 hours additional reagents (2 eq.) were necessary to complete reaction. Solvent was evaporated under vacuo and the residue loaded on cation exchange resin. The resin was washed with methanol and desired product was eluted with 2 N ammonia solution in methanol. Evaporation of appropriate fractions and further purification of the residue by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant) gave, after lyophilization, title compound as a white solid.

Workup

  1. customwere necessary to complete reaction
  2. customSolvent was evaporated under vacuo
  3. washThe resin was washed with methanol and desired product
  4. washwas eluted with 2 N ammonia solution in methanol
  5. customEvaporation of appropriate fractions and further purification of the residue by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant)
  6. customgave

Sources & evidence

ORD record
ord-b6eedf02450c46779a676d361f2eb53b
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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