Chloromethyl Methyl Ether → HCID 58101112, compound

HRID 536133Notes

Reaction equation

HRID 536133 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[N:18]([CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:17]3[CH:27]=[CH:28][CH:29]=[CH:30][C:16]=3[N:8]2[C:9](=[O:15])[C:10]=1[O:11][C:12](=[O:14])[CH3:13])=[O:4].C(N(C(C)C)CC)(C)C.[CH3:40][O:41][CH2:42]Cl>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]2[N:18]([CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][N:24]([CH2:40][O:41][CH3:42])[CH2:25][CH2:26]3)[C:17]3[CH:27]=[CH:28][CH:29]=[CH:30][C:16]=3[N:8]2[C:9](=[O:15])[C:10]=1[O:11][C:12](=[O:14])[CH3:13])=[O:4]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 58100971HCID 58100971, compound

Product 1

HCID 58101112HCID 58101112, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Acetoxy-4-oxo-10-(2-piperazin-1-yl-ethyl)-4,10-dihydro-benzo[4,5]imidazo[1,2-α]pyrimidine-2-carboxylic acid methyl ester (Example 15.3) (97 mg, 0.235 mmol) was dissolved in Dichloromethane (1 mL) and to it was added diisopropylethylamine (95 μL, 0.52 mmol), followed by methoxymethyl chloride (20 μA, 0.258 mmol). The reaction was stirred at room temperature for 24 h before the solvents were evaporated and the residue purified by column chromatography (98:1.5:0.5 dichloromethane: methanol: aqueous ammonia) to afford the desired product (30 mg, 28%).

Workup

  1. customwere evaporated
  2. customthe residue purified by column chromatography (98:1.5:0.5 dichloromethane: methanol: aqueous ammonia)

Sources & evidence

ORD record
ord-de0834b223e24b4ebda7d1807a8ce774
Source dataset
uspto-grants-2014_10
Patent number
US08859563B2

Reaction notes

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