Acetic Acid → (S)-Methyl 2-(4-((3-(2-amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)propylamino)methyl)phenyl)acetate

HRID 1617143Notes

Reaction equation

HRID 1617143 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:10][CH2:11][OH:12])[C:5]([CH2:17][CH2:18][CH2:19][NH2:20])=[C:4]([CH3:21])[N:3]=1.[CH3:22][O:23][C:24](=[O:34])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][CH:27]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:10][CH2:11][OH:12])[C:5]([CH2:17][CH2:18][CH2:19][NH:20][CH2:32][C:29]2[CH:28]=[CH:27][C:26]([CH2:25][C:24]([O:23][CH3:22])=[O:34])=[CH:31][CH:30]=2)=[C:4]([CH3:21])[N:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 19363032Methyl 2-(4-formylphenyl)acetateHCID 68416454(S)-3-(2-Amino-5-(3-aminopropyl)-6-methylpyrimidin-4-ylamino)heptan-1-ol

Product 1

HCID 42612994(S)-Methyl 2-(4-((3-(2-amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)propylamino)methyl)phenyl)acetateYield 3.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from step (ix) (57 mg) in THF (5 mL) was added (4-formylphenyl)acetic acid methyl ester (51 mg) and acetic acid (0.011 mL). The resulting mixture was stirred for 5 h, sodium triacetoxyborohydride (90 mg) was added and the resulting solution stirred at rt for 16 h. TEA (0.013 mL) was added and the reaction mixture stirred for a further 2 h. The solvents were evaporated, the residue redissolved in MeOH and purified by RPHPLC to afford the title compound 2.7 mg.

Workup

  1. stirringthe resulting solution stirred at rt for 16 h
  2. stirringthe reaction mixture stirred for a further 2 h
  3. customThe solvents were evaporated
  4. dissolutionthe residue redissolved in MeOH
  5. custompurified by RPHPLC

Sources & evidence

ORD record
ord-245aa0401cfd47aa8df410ad1fe05786
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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