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

HRID 2387863Notes

Reaction equation

HRID 2387863 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:19]=[C:20]([CH2:25][C:26]#[N:27])[CH:21]=[CH:22][C:23]=2[F:24])=[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:19]=[C:20]([CH2:25][C:26]#[N:27])[CH:21]=[CH:22][C:23]=2[F:24])=[C:12]([CH3:28])[N:11]=1

Participants

4

Reactant 2

HCID 11062353(S)-3-aminohexan-1-olHCID 866334102-(3-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-4-fluorophenyl)acetonitrile

Product 1

HCID 68956027(S)-2-(3-((2-Amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-4-fluorophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

(S)-3-Aminohexan-1-ol (101 mg) was added to a stirred solution of the product from step (iv) (100 mg) in butan-1-ol (2 mL). The reaction was performed in a microwave, at 180° C. for 2 h. The solvent was removed and the crude product was purified using chromatography, to give the subtitle compound, 70 mg.

Workup

  1. customThe solvent was removed
  2. customthe crude product was purified

Sources & evidence

ORD record
ord-adb6b575bb71403bb72ae6888547dc35
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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