Formaldehyde → HCID 68901576, compound

HRID 1986336Notes

Reaction equation

HRID 1986336 reaction equation
[CH2:1]=O.[CH3:3][NH:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[CH:14]=[C:13]([C:15]3[C:20]([CH3:21])=[CH:19][N:18]=[C:17]([NH:22][CH2:23][CH2:24][CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[N:16]=3)[S:12][C:11]=2[CH:31]=1)=[O:6].[BH4-].[Na+]>CO.ClCCl>[CH3:3][NH:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[CH:14]=[C:13]([C:15]3[C:20]([CH3:21])=[CH:19][N:18]=[C:17]([NH:22][CH2:23][CH2:24][CH:25]4[CH2:26][CH2:27][N:28]([CH3:1])[CH2:29][CH2:30]4)[N:16]=3)[S:12][C:11]=2[CH:31]=1)=[O:6]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 68857394HCID 68857394, compound

Product 1

HCID 68901576HCID 68901576, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Aqueous formaldehyde (37.4% or 13.5 M, 0.711 mL, 9.60 mmol) is added to a stirred solution of 2-[5-methyl-2-(2-piperidin-4-yl-ethylamino)-pyrimidin-4-yl]-benzo[b]thiophene-6-carboxylic acid methylamide (346 mg, 0.845 mmol) in CH3OH (10 mL) and dichloromethane (10 mL) at room temperature. The resultant mixture is stirred for 90 minutes. After being cooled to 0° C., the mixture is treated with powdered sodium borohydride (211 mg, 8.00 mmol) and stirred for 60 minutes. The mixture is allowed to stir at room temperature for 3 hours, concentrated and subject to chromatographic purification on silica gel, eluting with 2 M NH3/CH3OH in dichloromethane 0-8%, to give the title compound as a yellowish foam (280 mg, 78% yield). ES+(m/z) 424 [M+H].

Workup

  1. stirringto stir at room temperature for 3 hours
  2. concentrationconcentrated
  3. customsubject to chromatographic purification on silica gel
  4. washeluting with 2 M NH3/CH3OH in dichloromethane 0-8%

Sources & evidence

ORD record
ord-eb007c4149404878b10289e9373b366e
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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