(S)-3-aminohexan-1-ol → (S)-2-(4-((2-Amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetonitrile

HRID 2387873Notes

Reaction equation

HRID 2387873 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][CH3:8])[CH2:3][CH2:4][OH:5].[NH2:9][C:10]1[N:15]=[C:14](Cl)[C:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]#[N:26])=[CH:20][C:19]=2[F:27])=[C:12]([CH3:28])[N:11]=1>C(O)CCC>[NH2:9][C:10]1[N:15]=[C:14]([NH:1][C@@H:2]([CH2:6][CH2:7][CH3:8])[CH2:3][CH2:4][OH:5])[C:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]#[N:26])=[CH:20][C:19]=2[F:27])=[C:12]([CH3:28])[N:11]=1

Participants

4

Reactant 2

HCID 11062353(S)-3-aminohexan-1-olHCID 866334052-(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetonitrile

Product 1

HCID 68957878(S)-2-(4-((2-Amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

(S)-3-Aminohexan-1-ol (0.966 g) was added to a suspension of the product of example 33 step (iii) (1.2 g) in butan-1-ol (9 mL). The reaction was performed in the CEM Microwave, at 180° C. for 2 h. The solvent was evaporated under reduced pressure and the crude product was purified by flash silica chromatography, to give the subtitle compound as an orange solid, 0.98 g.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude product was purified by flash silica chromatography

Sources & evidence

ORD record
ord-dc692d80c69b43848daa9db96d463849
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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