5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde → 6-Cyclopentyl-3-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-6-[2-(3-ethyl-5-fluoro-4-hydroxy-phenyl)-ethyl]-4-hydroxy-5,6-dihydro-pyran-2-one

HRID 858637Notes

Reaction equation

HRID 858637 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([CH:12]=O)[N:11]=[C:4]2[N:3]=1.[CH:14]1([C:19]2([CH2:27][CH2:28][C:29]3[CH:34]=[C:33]([F:35])[C:32]([OH:36])=[C:31]([CH2:37][CH3:38])[CH:30]=3)[O:24][C:23](=[O:25])[CH2:22][C:21](=[O:26])[CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15]1>CO>[CH:14]1([C:19]2([CH2:27][CH2:28][C:29]3[CH:34]=[C:33]([F:35])[C:32]([OH:36])=[C:31]([CH2:37][CH3:38])[CH:30]=3)[O:24][C:23](=[O:25])[C:22]([CH2:12][C:10]3[N:11]=[C:4]4[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]4[N:9]=3)=[C:21]([OH:26])[CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 587627526-Cyclopentyl-6-[2-(3-ethyl-5-fluoro-4-hydroxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione

Product 1

HCID 587626986-Cyclopentyl-3-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-6-[2-(3-ethyl-5-fluoro-4-hydroxy-phenyl)-ethyl]-4-hydroxy-5,6-dihydro-pyran-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde (0.2 g, 0.57 mmol) was added to a solution of 6-Cyclopentyl-6-[2-(3-ethyl-5-fluoro-4-hydroxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione (0.2 g, 0.53 mmol) in MeOH (6 mL). The reaction mixture was stirred for 15 mins and then treated with borane-dimethylamine complex (50 mg, 0.86 mmoL). After 15 hours the reaction mixture was quenched with 1N HCl and extracted with 10% MeOH in CH2Cl2. The combined organic layers were concentrated and recrystallized from EtOAc to give the product as a white soild (0.15 g, 52%). 1H NMR (400 MHz, DMSO-d6): δ 1.09 (t, J=7.3 Hz, 3 H), 1.43–1.72 (br m, 8 H), 2.05–2.17 (m, 2 H), 2.43 (m, 1 H), 2.48–2.58 (m, 10 H), 2.66 (d, J=17.4 Hz, 1 H), 2.81 (d, J=17.4 Hz, 1 H), 3.74 (d, J=16.2 Hz, 1 H), 3.85 (d, J=16.2 Hz, 1 H), 6.76 (s, 1 H), 6.84 (d, J=11.6 Hz, 1 H) 7.07 (s, 1 H), 9.08 (s, 1 H), 11.01 (s, 1 H). MS: C28H32N4O4F (M+H+) 509.10.

Workup

  1. additiontreated with borane-dimethylamine complex (50 mg, 0.86 mmoL)
  2. customAfter 15 hours the reaction mixture was quenched with 1N HCl
  3. extractionextracted with 10% MeOH in CH2Cl2
  4. concentrationThe combined organic layers were concentrated
  5. customrecrystallized from EtOAc
  6. customto give the product as a white soild (0.15 g, 52%)

Sources & evidence

ORD record
ord-af71e1ebc4464dc9a1e1444053f6d11c
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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