6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde → HCID 58762198, compound

HRID 858675Notes

Reaction equation

HRID 858675 reaction equation
[Cl: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>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH2:11][C:21]3[C:22](=[O:24])[O:23][C:18]([CH:13]4[CH2:14][CH2:15][CH2:16][CH2:17]4)([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH2:35][C:36]([F:38])([F:39])[F:37])[CH:29]=4)[CH2:19][C:20]=3[OH:25])[N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 587625546-Chloro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 58762700HCID 58762700, compound

Product 1

HCID 58762198HCID 58762198, compoundYield 5.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-chloro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde (0.131 g, 0.72 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 (0.230 g, 0.60 mmol) in MeOH (10 mL). The reaction mixture was stirred for 15 mins and then treated with borane-dimethylamine complex (53 mg, 0.9 mmoL). After 15 hours the reaction mixture was quenched with concentrated HCl, and concentrated to a residual oil. Purification by flash column chromatography (EtOAc then 0%–5% MeOH in CH2Cl2) gave the product as a white solid (17 mg). 1H NMR (DMSO): δ 1.30–1.80 (brm, 8H), 2.08–2.18 (brm, 3H), 2.74 (s, 2H), 2.99(m, 2H); 3.15 (m, 2H), 3.47 (m, 3 H), 6.81 (m, 2H), 7.00(s, 1H), 8.76 (s, 1H), 8.82 (s, 1H). Anal. Calcd. For C26H26O4N4ClF3: C, 56.68; H, 4.75; N, 10.17. Found: C, 56.50; H, 4.69; N, 10.20.

Workup

  1. additiontreated with borane-dimethylamine complex (53 mg, 0.9 mmoL)
  2. customAfter 15 hours the reaction mixture was quenched with concentrated HCl
  3. concentrationconcentrated to a residual oil
  4. customPurification by flash column chromatography (EtOAc

Sources & evidence

ORD record
ord-0e5e5c49786143309aecff8b4027543d
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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