5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde → HCID 58764123, compound

HRID 1438278Notes

Reaction equation

HRID 1438278 reaction equation
[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:23][CH:24]=[CH:25][N:26]=4)=[C:18]([CH2:27][CH3:28])[CH:17]=3)[O:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C2(CCC3C=C(CC)C(O)=CC=3OCCC)OC(=O)CC(=O)C2)CCCC1.[CH3:57][C:58]1[CH:59]=[N:60][C:61]2[N:62]([N:64]=[C:65]([CH:67]=O)[N:66]=2)[CH:63]=1.CC1C=C(C)N2N=C(C=O)N=C2N=1>>[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:23][CH:24]=[CH:25][N:26]=4)=[C:18]([CH2:27][CH3:28])[CH:17]=3)[O:11][C:10](=[O:12])[C:9]([CH2:67][C:65]3[N:66]=[C:61]4[N:60]=[CH:59][C:58]([CH3:57])=[CH:63][N:62]4[N:64]=3)=[C:8]([OH:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 587626196-Methyl-[1,2,4]triazolo[1,5-A]pyrimidine-2-carbaldehydeHCID 587640596-cyclopentyl-6-{2-[3-ethyl-4-(1,3-oxazol-2-yl)phenyl]ethyl}dihydro-2H-pyran-2,4(3H)-dioneHCID 587641376-Cyclopentyl-6-[2-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione

Product 1

HCID 58764123HCID 58764123, compound

Procedure

The title compound was prepared analogously to example A(1) where 6-cyclopentyl-6-{2-[3-ethyl-4-(1,3-oxazol-2-yl)phenyl]ethyl}dihydro-2H-pyran-2,4(3H)-dione (Example A(135)) was substituted in place of 6-cyclopentyl-6-[2-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione in that example and 6-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde was substituted in place of 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde. Yield (58 mg, 11%). 1H NMR (300 MHz, CDCl3): δ ppm 1.19 (t, J=7.44 Hz, 3H) 1.40 (d, J=4.33 Hz, 1H) 1.53-1.67 (m, 8H) 2.01-2.10 (m, 2H) 2.39 (s, 1H) 2.45-2.49 (m, 3H) 2.54-2.64 (m, 1H) 2.71 (dd, J=11.87, 5.46 Hz, 2H) 2.76-2.85 (m, 1H) 3.01 (q, J=7.47 Hz, 2H) 4.10 (s, 2H) 7.05-7.11 (m, 2H) 7.29 (s, 1H) 7.73 (s, 1H) 7.78 (d, J=7.91 Hz, 1H) 8.61 (s, 1H) 8.68 (d, J=2.07 Hz, 1H). MS (ESI): 528 (M+H)+.

Workup

  1. customYield (58 mg, 11%)

Sources & evidence

ORD record
ord-5eb744159ce746929499441e8848b36f
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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