5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde → HCID 58762478, compound

HRID 858657Notes

Reaction equation

HRID 858657 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]([CH2:35][CH3:36])[CH:32]=[CH:31][C:30]=3[OH:37])[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]([CH2:35][CH3:36])[CH:32]=[CH:31][C:30]=3[OH:37])[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 58762360HCID 58762360, compound

Product 1

HCID 58762478HCID 58762478, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde (0.19 g, 1.1 mmol) was added to a solution of 6-cyclopentyl-6-[2-(5-ethyl-2-hydroxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione (0.3 g, 0.91 mmol Example A(169)) in MeOH (8 mL). The reaction mixture was stirred for 15 mins and then treated with borane-dimethylamine complex (47 mg, 0.80 mmoL). After 24 hours the reaction mixture was filtered through a glass frit to remove a fine white ppt. The filtrate was concentrated and purified by prep HPLC to give the product (175 mg, 40%). 1H NMR (400 MHz, DMSO-d6) δ: 1.07 (t, J=7.6 Hz, 3 H), 1.41–1.72 (br m, 8 H), 1.97 (m, 1 H), 2.10 (m, 1 H), 2.41–2.73 (m, 13 H), 3.70 (d, J=16.2 Hz, 1 H), 3.79 (d, J=16.2 Hz, 1 H), 6.66 (d, J=8.1 Hz, 1 H), 6.81 (d, J=8.1 Hz, 1 H), 6.84 (s, 1 H), 7.02 (s, 1 H), 9.02 (s, 1 H), 10.88 (s, 1 H). MS (ESI): 491.20 (M+H+).

Workup

  1. additiontreated with borane-dimethylamine complex (47 mg, 0.80 mmoL)
  2. filtrationAfter 24 hours the reaction mixture was filtered through a glass frit
  3. customto remove a fine white ppt
  4. concentrationThe filtrate was concentrated
  5. custompurified by prep HPLC

Sources & evidence

ORD record
ord-4b6a949352154dada9ed1f11d1623228
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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