Sodium borohydride → [4-({[3-(6-Amino-2-butoxy-8-methoxy-9H-purin-9-yl)propyl]amino}methyl)phenyl]acetic acid

HRID 1095327Notes

Reaction equation

HRID 1095327 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]([O:14][CH3:15])=[N:12][C:11]2[C:6]1=[N:7][C:8]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[N:9][C:10]=2[NH2:16].[CH:22]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([OH:33])=[O:32])=[CH:26][CH:25]=1)=O.[BH4-].[Na+]>C1COCC1.CO>[NH2:16][C:10]1[N:9]=[C:8]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])[N:7]=[C:6]2[C:11]=1[N:12]=[C:13]([O:14][CH3:15])[N:5]2[CH2:4][CH2:3][CH2:2][NH:1][CH2:22][C:24]1[CH:25]=[CH:26][C:27]([CH2:30][C:31]([OH:33])=[O:32])=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 113441872-(4-formylphenyl)acetic AcidHCID 231585469-(3-Aminopropyl)-2-butoxy-8-methoxy-9H-purin-6-amine

Product 1

HCID 66781394[4-({[3-(6-Amino-2-butoxy-8-methoxy-9H-purin-9-yl)propyl]amino}methyl)phenyl]acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The product from step (vii) (9.7 g) and (4-formylphenyl)acetic acid (5.4 g) were dissolved in THF (100 ml) and stirred at rt for 4 h. Sodium borohydride (1.9 g) and 5 drops of methanol was added and stirred at a rt overnight. The mixture was quenched with water and concentrated under reduced pressure. Water was added and washed with diethyl ether. 0.1N—HCl was added to acidify the solution to pH 6. The suspension was filtered and the solid collected and dried under reduced pressure to give the subtitle compound. Yield 13 g.

Workup

  1. stirringstirred at a rt overnight
  2. customThe mixture was quenched with water
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added
  5. washwashed with diethyl ether
  6. addition0.1N—HCl was added
  7. filtrationThe suspension was filtered
  8. customthe solid collected
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-e10b7082a4f24b19882071410c319e22
Source dataset
uspto-grants-2012_03
Patent number
US08138172B2

Reaction notes

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