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Formaldehyde → 1-(5-Cyano-pyrazin-2-yl)-3-[5-methyl-2-(4-methyl-morpholin-2-ylmethoxy)-phenyl]-urea

HRID 418010
Notes
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Reaction equation

HRID 418010 reaction equation
Cl.[C:2]([C:4]1[N:5]=[CH:6][C:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=2[O:21][CH2:22][CH:23]2[O:28][CH2:27][CH2:26][NH:25][CH2:24]2)=[O:12])=[N:8][CH:9]=1)#[N:3].C=O.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[C:2]([C:4]1[N:5]=[CH:6][C:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=2[O:21][CH2:22][CH:23]2[O:28][CH2:27][CH2:26][N:25]([CH3:31])[CH2:24]2)=[O:12])=[N:8][CH:9]=1)#[N:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 666489091-(5-Cyano-pyrazin-2-yl)-3-[5-methyl-2-(morpholin-2-ylmethoxy)-phenyl]-urea hydrochloride salt

Product 1

HCID 119559831-(5-Cyano-pyrazin-2-yl)-3-[5-methyl-2-(4-methyl-morpholin-2-ylmethoxy)-phenyl]-ureaYield 28.4%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

A solution of 1-(5-cyano-pyrazin-2-yl)-3-[5-methyl-2-(morpholin-2-ylmethoxy)-phenyl]-urea hydrochloride salt (0.0104 g, 0.129 mmol) in MeOH (1 mL) was cooled to 0° C. and treated with an aqueous solution of formaldehyde (0.12 mmol) followed by sodium triacetoxy borohydride (0.06 g, 0.292 mmol). The reaction was stirred for 12 h, then concentrated in vacuo. The residue was chromatographed on silica (2% MeOH in CH2Cl2) to give the product as a white solid (0.014 g). 1H-NMR (400 MHz, d6-DMSO) δ 10.90 (s, 1, H), 10 (br s, 1, H), 8.9 (s, 1, H), 8.8 (s, 1, H), 8 (s, 1, H), 6.9 (m, 1, H), 6.8 μm, 1, H), 3.9 (m, 4, H), 3.6 (t, 1, H), 2.9 (d, 1, H), 2.7 (d, 1, H), 2.2 (s, 3, H), 2.1 (s, 3, H), 2 (t, 1, H), 1.8 (t, 1, H). LRMS (esi, positive) m/e 383.40 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed on silica (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-015e8e4c2a4d44c39a1c1302b20e1a94
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08093244B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes