6-Methyl-[1,2,4]triazolo[1,5-A]pyrimidine-2-carbaldehyde → HCID 58762196, compound

HRID 858676Notes

Reaction equation

HRID 858676 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH:11]=O)[N:10]=2)[CH:7]=1.[CH:13]1([C:18]2([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH2:35][C:36]([F:39])([F:38])[F:37])[CH:29]=3)[O:23][C:22](=[O:24])[CH2:21][C:20](=[O:25])[CH2:19]2)[CH2:17][CH2:16][CH2:15][CH2:14]1>CO>[CH:13]1([C:18]2([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH2:35][C:36]([F:39])([F:37])[F:38])[CH:29]=3)[O:23][C:22](=[O:24])[C:21]([CH2:11][C:9]3[N:10]=[C:5]4[N:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]4[N:8]=3)=[C:20]([OH:25])[CH2:19]2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 587626196-Methyl-[1,2,4]triazolo[1,5-A]pyrimidine-2-carbaldehydeHCID 58762700HCID 58762700, compound

Product 1

HCID 58762196HCID 58762196, compoundYield 20.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde (0.88 g, 0.546 mmol) was added to a solution of example A(228) 6-cyclopentyl-6-{2-[4-hydroxy-3-(2,2,2-trifluoroethyl)phenyl]ethyl}dihydro-2H-pyran-2,4(3H)-dione (0.175 g, 0.455 mmol) and borane-dimethylamine complex (53 mg, 0.9 mmoL) in MeOH (10 mL). The reaction was stirred at room temperature for 15 hours, after which time the mixture was concentrated to a residual oil, and purified by preparatory HPLC to afford the title compound as a white solid (50 mg). 1H NMR (DMSO): δ 1.35–1.85 (brm, 8H), 2.00–2.20 (brm, 3H), 2.50 (s, 3H), 2.74 (s, 2H), 2.99(m, 2H); 3.04 (m, 2H), 3.54 (m, 3H), 6.81 (m, 2H), 7.00(s, 1H), 8.55 (s, 1H), 8.72 (s, 1H). Anal. Calcd. For C27H29O4N4F3: C, 61.14; H, 5.51; N, 9.06. Found: C, 61.21; H, 5.60; N, 9.14.

Workup

  1. concentrationafter which time the mixture was concentrated to a residual oil
  2. custompurified by preparatory HPLC

Sources & evidence

ORD record
ord-7840a72ec30a4205984be44db1e8f04c
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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