Acetic Acid → Methyl 2-(3-((4-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)butylamino)methyl)phenyl)acetate

HRID 2387786Notes

Reaction equation

HRID 2387786 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:7]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[N:8][C:9]([NH2:13])=[N:10][C:11]=1[CH3:12].[CH:20]([C:22]1[CH:23]=[C:24]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:25]=[CH:26][CH:27]=1)=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[NH2:13][C:9]1[N:10]=[C:11]([CH3:12])[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][CH2:20][C:22]2[CH:23]=[C:24]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:25]=[CH:26][CH:27]=2)=[C:7]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 11819590Methyl 2-(3-formylphenyl)acetateHCID 684176515-(4-Aminobutyl)-6-methyl-N4-pentylpyrimidine-2,4-diamine

Product 1

HCID 42612993Methyl 2-(3-((4-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)butylamino)methyl)phenyl)acetateYield 6.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the product of step (ii) (0.06 g), methyl 2-(3-formylphenyl)acetate (0.0403 g) and acetic acid (0.0136 g) in THF (10 mL) was added sodium triacetoxyborohydride (0.1102 g). The reaction mixture was stirred for 72 h, the solvents were evaporated and the residue dissolved in MeOH, acidified and purified via SCX resin, then RPHPLC to give the title compound 6 mg.

Workup

  1. customthe solvents were evaporated
  2. dissolutionthe residue dissolved in MeOH
  3. custompurified via SCX resin

Sources & evidence

ORD record
ord-cfb2313995c9489992d95ee3d95d3961
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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