Formaldehyde → HCID 54698255, compound

HRID 1012983Notes

Reaction equation

HRID 1012983 reaction equation
N[C:2]([C:5]1[N:10]=[C:9]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[S:22]([CH3:25])(=[O:24])=[O:23])=[O:12])[C:8]([OH:26])=[C:7]([OH:27])[N:6]=1)([CH3:4])[CH3:3].[CH2:28]=O.[C:30]([BH3-])#[N:31].[Na+]>C(OC)(OC)OC.C(O)(=O)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][NH:13][C:11]([C:9]2[N:10]=[C:5]3[C:2]([CH3:3])([CH3:4])[N:31]([CH3:30])[CH2:28][N:6]3[C:7](=[O:27])[C:8]=2[OH:26])=[O:12])=[C:16]([S:22]([CH3:25])(=[O:23])=[O:24])[CH:17]=1

Participants

6

Reactant 3

HCID 712Formaldehyde2×HCID 5003444Sodium cyanoborohydrideHCID 178456882HCID 178456882, compound

Product 1

HCID 54698255HCID 54698255, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 9005Trimethyl orthoformateSolvent

Procedure

2-(1-amino-1-methylethyl)-N-[4-fluoro-2-(methylsulfonyl)benzyl]-5,6-dihydroxypyrimidine-4-carboxamide (prepared as described in WO2003035076 A1) was taken in trimethyl orthoformate and treated with 1.1 eq. of formaldehyde. The mixture was aged at room temperature for 1 hour, and then an additional equivalent of formaldehyde was added, followed by 1.5 eq. of sodium cyanoborohydride and a few drops of acetic acid. Stirring was continued for one hour more, and the mixture was purified by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant) to afford the title compound as a white solid.

Workup

  1. waitwas continued for one hour
  2. custommore, and the mixture was purified by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant)

Sources & evidence

ORD record
ord-8ef61a30af8c43d08791ec7f060f91a8
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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