(S)-3-aminoheptan-1-ol → (S)-tert-Butyl 3-(2-amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)prop-2-ynylcarbamate

HRID 2387793Notes

Reaction equation

HRID 2387793 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]#[C:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[C:4]([CH3:20])[N:3]=1.[NH2:21][C@@H:22]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:23][CH2:24][OH:25]>C(O)CCC>[NH2:1][C:2]1[N:7]=[C:6]([NH:21][C@@H:22]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:23][CH2:24][OH:25])[C:5]([C:9]#[C:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[C:4]([CH3:20])[N:3]=1

Participants

4

Reactant 2

HCID 55290391(S)-3-aminoheptan-1-olHCID 86633394tert-Butyl 3-(2-amino-4-chloro-6-methylpyrimidin-5-yl)prop-2-ynylcarbamate

Product 1

HCID 86633395(S)-tert-Butyl 3-(2-amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)prop-2-ynylcarbamateYield 64.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

The product from step (vi) (200 mg) and the product from step (v) (177 mg) were combined in butan-1-ol (5 mL) and reacted in a CEM Microwave, at 120° C. for 1 h. The solvents were evaporated, and the crude product was purified by chromatography, eluting with 5% MeOH in EtOAc to afford the subtitle compound 170 mg.

Workup

  1. customreacted in a CEM Microwave, at 120° C. for 1 h
  2. customThe solvents were evaporated
  3. customthe crude product was purified by chromatography
  4. washeluting with 5% MeOH in EtOAc

Sources & evidence

ORD record
ord-3697877e14f74c54a0a642a940226da5
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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