1-Bromopropane → HCID 10204345, compound

HRID 271619Notes

Reaction equation

HRID 271619 reaction equation
[H-].[Na+].C1OCCOCCOCCOCCOCCOC1.[CH3:21][C:22]([CH3:50])([CH3:49])[CH2:23][N:24]1[C:28]2[N:29]=[C:30]([C:33]#[N:34])[N:31]=[CH:32][C:27]=2[CH:26]=[C:25]1[CH2:35][N:36]1[C:40](=[O:41])[C:39]2([CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)[N:38]([CH3:47])[C:37]1=[O:48].Br[CH2:52][CH2:53][CH3:54]>CN(C=O)C>[CH3:21][C:22]([CH3:50])([CH3:49])[CH2:23][N:24]1[C:28]2[N:29]=[C:30]([C:33]#[N:34])[N:31]=[CH:32][C:27]=2[CH:26]=[C:25]1[CH2:35][N:36]1[C:40](=[O:41])[C:39]2([CH2:42][CH2:43][N:44]([CH2:52][CH2:53][CH3:54])[CH2:45][CH2:46]2)[N:38]([CH3:47])[C:37]1=[O:48]

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 59834617HCID 59834617, compound

Product 1

HCID 10204345HCID 10204345, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 27.4 mg (0.685 mmoles) of NaH and 6.5 mg (0.025 mmoles) of 18-crown-6 in 2.0 ml of DMF, 200 mg (0.488 mmoles) of 7-(2,2-Dimethyl-propyl)-6-(1-methyl-2,4-dioxo-1,3,8-triaza-spiro[4.5]dec-3-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile is added at ambient temperature. After being stirred for 10 minutes, 75□l (0.823 mmoles) of 1-bromo propane is added at 0° C. and the reaction mixture is stirred for 5 hours at ambient temperature. The reaction mixture is quenched with cold H2O and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated reduced pressure. The residue is purified by silica gel column chromatography to give 90.5 mg of desired 7-(2,2-dimethyl-propyl)-6-(1-methyl-2,4-dioxo-8-propyl-1,3,8-triaza-spiro[4.5]dec-3-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 41% yield.

Workup

  1. additionis added at ambient temperature
  2. stirringthe reaction mixture is stirred for 5 hours at ambient temperature
  3. customThe reaction mixture is quenched with cold H2O
  4. extractionextracted with AcOEt
  5. washThe combined extracts are washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated reduced pressure
  8. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-445fbc15b7894f0ba9b2dfdd78199166
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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