Sodium hydride → HCID 86637534, compound

HRID 1099107Notes

Reaction equation

HRID 1099107 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][O:4][CH2:3]1.[H-].[Na+].Cl[C:10]1[C:11]2[N:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:12]=2[N:13]=[C:14]([NH:16]C(=O)C)[N:15]=1>C1COCC1>[Cl:24][C:22]1[CH:21]=[CH:20][C:12]2[N:13]=[C:14]([NH2:16])[N:15]=[C:10]([O:1][CH:2]3[CH2:6][CH2:5][O:4][CH2:3]3)[C:11]=2[N:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 641512(-)-3-HydroxytetrahydrofuranHCID 57698319N-(4,6-Dichloropyrido[3,2-d]pyrimidin-2-yl)acetamide

Product 1

HCID 86637534HCID 86637534, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(R)-(−)-3-hydroxy-tetrahydrofuran (0.62 mL) was added to a suspension of NaH (0.31 g, 7.7 mmol) in THF (15 mL). After stirring for 1 hour, the resulting mixture was added to a suspension of N-(4,6-dichloro-pyrido[3,2-d]pyrimidin-2-yl)-acetamide (0.9 g, 3.5 mmol) in THF (15 mL). The mixture was stirred at room temperature for 20 minutes, then diluted with EtOAC (100 mL) and washed with brine. The organic layer was dried over Na2SO4 and concentrated to afford 6-chloro-4-(tetrahydro-furan-3-yloxy)-pyrido[3,2-d]pyrimidin-2-ylamine as a yellow solid (0.55 g, yield: 51%) which was characterized by its mass spectrum as follows: MS (m/z) 309.1 [M+H]+.

Workup

  1. stirringThe mixture was stirred at room temperature for 20 minutes
  2. additiondiluted with EtOAC (100 mL)
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9c8f69c9c93c4ea29e2512d97429a096
Source dataset
uspto-grants-2012_03
Patent number
US08143394B2

Reaction notes

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