Sodium hydride → HCID 66639747, compound

HRID 1094052Notes

Reaction equation

HRID 1094052 reaction equation
[NH2:1][C:2]1[C:3]([C:28]#[N:29])=[C:4]([C:16]2[CH:21]=[C:20]([O:22][CH2:23][CH3:24])[CH:19]=[C:18]([O:25][CH2:26][CH3:27])[CH:17]=2)[C:5]2[C:10](=[O:11])[N:9]([CH3:12])[C:8](=[O:13])[N:7]([CH3:14])[C:6]=2[N:15]=1.[H-].[Na+].Br[CH2:33][C:34]1[CH:43]=[CH:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=1>CN(C=O)C>[CH2:26]([O:25][C:18]1[CH:17]=[C:16]([C:4]2[C:5]3[C:10](=[O:11])[N:9]([CH3:12])[C:8](=[O:13])[N:7]([CH3:14])[C:6]=3[N:15]=[C:2]([NH:1][CH2:33][C:34]3[CH:43]=[CH:42][C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH:35]=3)[C:3]=2[C:28]#[N:29])[CH:21]=[C:20]([O:22][CH2:23][CH3:24])[CH:19]=1)[CH3:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 703202-BromomethylnaphthaleneHCID 66639754HCID 66639754, compound

Product 1

HCID 66639747HCID 66639747, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 56d (100 mg, 0.25 mmol) in DMF (3 mL) was treated with 60% NaH (12 mg, 0.3 mmol). After the mixture was vigorously stirred for 30 min, a solution of 2-(bromomethyl)naphthalene (55 mg, 0.25 mmol) was added. The mixture was stirred at rt for 20 min, and 50° C. for 2 h. After which the solution was suspended in 200 mL of EtoAce and was washed with brine, 3×200 mL. The organic layer was dried over Na2SO4 and evaporated in vacuuo. The residue was purified by prep HPLC to give 5-(3,5-diethoxyphenyl)-1,3-dimethyl-7-(naphthalene-2-ylmethylamino)-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine-6-carbonitrile (56e, 87 mg). MS [m+H] calc'd for C31H29N5O4, 536.22; found 536.22

Workup

  1. stirringThe mixture was stirred at rt for 20 min
  2. wait50° C. for 2 h
  3. washwas washed with brine, 3×200 mL
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated in vacuuo
  6. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-b04478a207144916a92b4466f12b9061
Source dataset
uspto-grants-2012_03
Patent number
US08133898B2

Reaction notes

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