Sodium → HCID 178489617, compound

HRID 1066499Notes

Reaction equation

HRID 1066499 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][CH:6]([C:11]([O:13]C)=O)[C:7]([O:9]C)=O.[Na].F[B-](F)(F)F.[CH2:25]([O:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=1)[C:36]([NH2:38])=[NH:37])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO>[CH2:25]([O:32][C:33]1[CH:34]=[C:35]([C:36]2[N:38]=[C:7]([OH:9])[C:6]([O:5][C:4]3[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=3[O:2][CH3:1])=[C:11]([OH:13])[N:37]=2)[CH:39]=[CH:40][CH:41]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 12967085Dimethyl 2-(2-methoxyphenoxy)malonateHCID 86756993HCID 86756993, compound

Product 1

HCID 178489617HCID 178489617, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

6.3 g of dimethyl (2-methoxyphenoxy)malonate were added dropwise within 5 minutes under an argon atmosphere to a solution of 1.72 g of sodium in methanol (150 ml) at 5° C. Stirring was continued for 30 minutes (5° C.) then 7.85 g of m-benzyloxy-benzamidine tetrafluoroborate in methanol (50 ml) were added within 5 minutes at 5° C. and the mixture was then stirred for further 20 h at RT. The solvent was removed in vacuo and the residue partitioned between water and EtOAc (each 50 ml). The cold aqueous phase was acidified dropwise with conc. HCl the precipitate filtered off under suction, washed with water and dried under reduced pressure to give the desired 2-(3-benzyloxy-phenyl)-5-(2-methoxy-phenoxy)-pyrimidine-4,6-diol as an off-white solid, mp 192°-195° C.

Workup

  1. stirringthe mixture was then stirred for further 20 h at RT
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between water and EtOAc (each 50 ml)
  4. filtrationfiltered off under suction
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-83698840eccf45ba82b288b0f362ae2a
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Reaction notes

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