Sodium hydride → HCID 86688463, compound

HRID 1422681Notes

Reaction equation

HRID 1422681 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-a12a7d5e3b9e4cbd9d35150831789eef
Source dataset
uspto-grants-2015_01
Patent number
US08927543B2

Reaction notes

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