Sodium Bicarbonate → Methyl 2-(3-((3-(2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylamino)methyl)phenyl)acetate

HRID 1617124Notes

Reaction equation

HRID 1617124 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[C:6]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[N:7][C:8]([NH2:12])=[N:9][C:10]=1[CH3:11].[CH:19]([C:21]1[CH:22]=[C:23]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:24]=[CH:25][CH:26]=1)=O.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.CO.C(O)(=O)C>[NH2:12][C:8]1[N:9]=[C:10]([CH3:11])[C:5]([CH2:4][CH2:3][CH2:2][NH:1][CH2:19][C:21]2[CH:22]=[C:23]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:24]=[CH:25][CH:26]=2)=[C:6]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:7]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride3×HCID 98378705-(3-Aminopropyl)-6-methyl-N4-pentylpyrimidine-2,4-diamineHCID 11819590Methyl 2-(3-formylphenyl)acetate

Product 1

HCID 42613957Methyl 2-(3-((3-(2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)propylamino)methyl)phenyl)acetate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from step (v) (Ig) was dissolved in THF (30 mL) then acetic acid (0.239 g, 0.23 ml) and methyl 2-(3-formylphenyl)acetate (0.709 g) were added followed by MeOH (0.5 mL). The reaction mixture was stirred at rt for 72 h then sodium borohydride (0.1506 g) was added. After 2 h a further portion of sodium borohydride (0.0452 g) was added and the reaction mixture stirred for 16 h. A further portion of sodium borohydride (0.1506 g) was added and stirred for 2 h. The reaction mixture was poured into saturated sodium bicarbonate solution and extracted with EtOAc. The solvents were evaporated and the product was purified by chromatography eluting with DCM:MeOH 97:3 to 80:20 to give the title compound 0.5 g.

Workup

  1. stirringthe reaction mixture stirred for 16 h
  2. stirringstirred for 2 h
  3. extractionextracted with EtOAc
  4. customThe solvents were evaporated
  5. customthe product was purified by chromatography
  6. washeluting with DCM:MeOH 97:3 to 80:20

Sources & evidence

ORD record
ord-1beb6012d0bf40bfab5c224c6a25de55
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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