Formaldehyde → HCID 73214470, compound

HRID 2200901Notes

Reaction equation

HRID 2200901 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:5][NH:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[O:14])=[CH:11][N:10]=[C:9]([N:24]2[CH2:30][CH2:29][C:26]3([CH2:28][CH2:27]3)[CH2:25]2)[N:8]=1.C=O.[BH4-].[Na+].[CH2:40](Cl)Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:5][NH:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][N:21]([CH3:40])[CH2:22][CH2:23]2)=[O:14])=[CH:11][N:10]=[C:9]([N:24]2[CH2:30][CH2:29][C:26]3([CH2:27][CH2:28]3)[CH2:25]2)[N:8]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 73214396HCID 73214396, compound

Product 1

HCID 73214470HCID 73214470, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (10 mL) was dissolved 4-((3-chloro-4-methoxybenzyl)amino)-N-(2-(piperazin-1-yl)ethyl)-2-(5-azaspiro[2.4]heptan-5-yl)pyrimidine-5-formamide (250 mg, 0.5 mmol). Formalin (37%, 61 mg, 0.75 mmol) was added. The reaction was conducted at ambient temperature for 1 h. Sodium borohydride (28 mg, 0.75 mmol) was added. The reaction was continued for 8 h, followed by addition of DCM (50 mL). The reaction mixture was washed with water for three times (50 mL at a time). The organic phase was dried and concentrated to give 4-((3-chloro-4-methoxybenzyl)amino)-N-[2-(4-methylpiperazin-1-yl)ethyl]-2-(5-azaspiro[2.4]heptan-5-yl)pyrimidine-5-formamide (168 mg, 65% yield). The product was dissolved in methanol (5 mL). Hydrochloric acid (0.1 mL) was added. The reaction mixture was stirred at ambient temperature for 30 min. The solvent was removed by evaporation to give the hydrochloride salt of the compound as a white solid.

Workup

  1. waitThe reaction was continued for 8 h
  2. washThe reaction mixture was washed with water for three times (50 mL at a time)
  3. customThe organic phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-707ef4fca5b6442ca9608776a927dfa3
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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