Sodium hydride → HCID 86688463, compound

HRID 1773299Notes

Reaction equation

HRID 1773299 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH2:7][OH:8].[H-].[Na+].Cl[C:12]1[CH:27]=[C:16]2[C:17]3[C:22]([CH2:23][CH2:24][N:15]2[C:14](=[O:28])[N:13]=1)=[CH:21][C:20]([O:25][CH3:26])=[CH:19][CH:18]=3>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH2:7][O:8][C:12]1[CH:27]=[C:16]2[C:17]3[C:22]([CH2:23][CH2:24][N:15]2[C:14](=[O:28])[N:13]=1)=[CH:21][C:20]([O:25][CH3:26])=[CH:19][CH:18]=3

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12655091(1,4-Dioxan-2-yl)methanolHCID 575910932-chloro-9-methoxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one

Product 1

HCID 86688463HCID 86688463, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[1,4]Dioxan-2-yl-methanol (42 mg, 0.36 mmol, 2 eq.) was dissolved in DCM (3 mL) with NaH (14 mg, 0.36 mmol, 2 eq., 60% in mineral oil). After 30 min, intermediate 38 (50 mg, 0.18 mmol, 1 eq.) was added to the mixture and the reaction was stirred at RT for 16 h. The reaction mixture was evaporated to dryness and the crude product was purified by preparative HPLC-MS to provide compound 162.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe crude product was purified by preparative HPLC-MS

Sources & evidence

ORD record
ord-9e581daf5569452299336e76d3a51132
Source dataset
uspto-grants-2016_02
Patent number
US09255095B2

Reaction notes

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