Sodium borohydride → HCID 67297519, compound

HRID 628991Notes

Reaction equation

HRID 628991 reaction equation
[BH4-].[Na+].C([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][CH3:16])=[C:12]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:11]=[C:10]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)[N:9]=1)=O)C>CCO>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:10]2[N:9]=[C:8]([CH2:6][OH:5])[C:13]([O:14][CH2:15][CH3:16])=[C:12]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[N:11]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67295455HCID 67295455, compound

Product 1

HCID 67297519HCID 67297519, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (192 mg, 5 eq.) was added to a stirred solution of 2-(4-amino-phenyl)-5-ethoxy-6-morpholin-4-yl-pyrimidine-4-carboxylic acid ethyl ester (378 mg, 1 eq.) in EtOH (12 ml) and the mixture reacted to reflux overnight. The mixture was quenched with H2O, the solvent removed in vacuo, and the residue extracted with EA and washed with brine. The crude was purified by chromatography to give a product (267 mg, 80%).

Workup

  1. customthe mixture reacted
  2. temperatureto reflux overnight
  3. customThe mixture was quenched with H2O
  4. customthe solvent removed in vacuo
  5. extractionthe residue extracted with EA
  6. washwashed with brine
  7. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-afc481ffc0714cf6b01b5560001082d2
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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