(2S)-2-aminopentan-1-ol → (S)-2-(4-((2-Amino-4-(1-hydroxypentan-2-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

HRID 2387828Notes

Reaction equation

HRID 2387828 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH2:6][CH3:7])[CH2:3][OH:4].[NH2:8][C:9]1[N:14]=[C:13](Cl)[C:12]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]#[N:25])=[CH:19][C:18]=2[O:26][CH3:27])=[C:11]([CH3:28])[N:10]=1>CN1C(=O)CCC1.CCOC(C)=O>[NH2:8][C:9]1[N:14]=[C:13]([NH:1][C@@H:2]([CH2:5][CH2:6][CH3:7])[CH2:3][OH:4])[C:12]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]#[N:25])=[CH:19][C:18]=2[O:26][CH3:27])=[C:11]([CH3:28])[N:10]=1

Participants

5

Reactant 2

HCID 6951248(2S)-2-aminopentan-1-olHCID 866334022-(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

Product 1

HCID 68955240(S)-2-(4-((2-Amino-4-(1-hydroxypentan-2-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

(S)-2-Aminopentan-1-ol (0.136 g) was added to a solution of the product from step (iii) in NMP (2 mL). The resulting mixture was stirred at 140° C. for 50 h then diluted with EtOAc and washed with saturated NaHCO3 solution and saturated brine. The organic phase was dried, filtered and evaporated. The crude product was purified by column chromatography, elution gradient 5 to 10% MeOH in DCM to give the subtitle compound, 0.095 g.

Workup

  1. washwashed with saturated NaHCO3 solution and saturated brine
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by column chromatography, elution gradient 5 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-9d136f7298c34c26b509ea9f118b1498
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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