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Lithium hexamethyldisilazane → (racemic) N-(5-chloro-4-((tetrahydrofuran-3-yl)oxy)pyrimidin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

HRID 1777874
Notes
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Reaction equation

HRID 1777874 reaction equation
[CH3:1][O:2][CH:3]([O:23][CH3:24])[C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14]([O:16]C2C=CC=CC=2)=O)=[CH:6][CH:5]=1.[Cl:25][C:26]1[C:27]([O:33][CH:34]2[CH2:38][CH2:37][O:36][CH2:35]2)=[N:28][C:29]([NH2:32])=[N:30][CH:31]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Cl:25][C:26]1[C:27]([O:33][CH:34]2[CH2:38][CH2:37][O:36][CH2:35]2)=[N:28][C:29]([NH:32][C:14]([N:11]2[C:12]3[C:7](=[CH:6][CH:5]=[C:4]([CH:3]([O:2][CH3:1])[O:23][CH3:24])[N:13]=3)[CH2:8][CH2:9][CH2:10]2)=[O:16])=[N:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2733832Lithium hexamethyldisilazaneHCID 808765925-Chloro-4-((tetrahydrofuran-3-yl)oxy)pyrimidin-2-amine2×HCID 118037161phenyl 7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate2×

Product 1

HCID 118037013(racemic) N-(5-chloro-4-((tetrahydrofuran-3-yl)oxy)pyrimidin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of phenyl 7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate (intermediate 3, 11.4 mg, 0.035 mmol) and 5-chloro-4-((tetrahydrofuran-3-yl)oxy)pyrimidin-2-amine (intermediate 30, 7.5 mg, 0.035 mmol) in THF (1.5 ml) at room temperature under argon was treated drop wise with LHMDS (1 M in THF, 0.10 ml, 0.10 mmol). The reaction mixture was stirred for 20 min, quenched by addition of sat. aq. NH4Cl and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound as a white solid. (UPLC-MS 3) tR 1.10 min; ESI-MS 450.1 [M+H]+.

Workup

  1. customquenched by addition of sat. aq. NH4Cl
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100)

Sources & evidence

ORD record
ord-28418b1d134d4340b602983a00ef356d
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266883B2

Reaction notes

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