3-Bromo-1-propanol → HCID 16124587, compound

HRID 1893922Notes

Reaction equation

HRID 1893922 reaction equation
[Br:1][C:2]1[C:15](=[O:16])[NH:14][C:5]2[N:6]=[C:7]([NH:11][CH2:12][CH3:13])[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1.[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][OH:23]>CN(C=O)C>[Br:1][C:2]1[C:15](=[O:16])[N:14]([CH2:20][CH2:21][CH2:22][OH:23])[C:5]2[N:6]=[C:7]([NH:11][CH2:12][CH3:13])[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 24758Sodium hydrideHCID 57930759HCID 57930759, compound

Product 1

HCID 16124587HCID 16124587, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-2-(ethylamino)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (100 mg, 0.35 mmol) in DMF (2 mL), prepared using procedures analogous to those described in Example 14, was added NaH (30 mg, 60%, 0.7 mmol). The mixture was stirred for 30 min at room temperature and was warmed to 70° C. 3-Bromopropanol (48 mg, 0.35 mmol) was then added. The stirring was continued for 12 h. Standard workup and purification by column chromatography gave 33 mg (27% yield) of 6-bromo-2-(ethylamino)-8-(3-hydroxypropyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one. 1H NMR (400 MHz, CDCl3) δ 8.13 (s, 1H), 5.42 (br s, 1H), 4.59 (br s, 2H), 3.50-3.47 (m, 5H), 2.55 (s, 3H), 2.02 (br s, 2H), 1.28 (t, 3H); MS (EI) for C13H17BrN4O2: 341 (MH+).

Workup

  1. temperaturewas warmed to 70° C
  2. waitThe stirring was continued for 12 h
  3. customStandard workup and purification by column chromatography

Sources & evidence

ORD record
ord-46d3a2a9839b43be814a2b1dafb12153
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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