(R)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one → HCID 58405738, compound

HRID 44895Notes

Reaction equation

HRID 44895 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C@@H:6]([CH2:14][CH3:15])[N:5]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:4]=2[N:3]=1.[S:21]1[CH:25]=[CH:24][N:23]=[C:22]1[C:26]1[N:30](COCC[Si](C)(C)C)[N:29]=[CH:28][C:27]=1B(O)O>>[CH:20]1([CH:16]([N:5]2[C:4]3[N:3]=[C:2]([C:27]4[CH:28]=[N:29][NH:30][C:26]=4[C:22]4[S:21][CH:25]=[CH:24][N:23]=4)[N:11]=[CH:10][C:9]=3[N:8]([CH3:12])[C:7](=[O:13])[C@H:6]2[CH2:14][CH3:15])[CH3:17])[CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 24820413(R)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-oneHCID 58405547HCID 58405547, compound

Product 1

HCID 58405738HCID 58405738, compound

Procedure

The title compound was prepared similarly to the methods described in Example 5, with Intermediate SS instead of Intermediate B and with 5-(thiazol-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-ylboronic acid (Boronic Acid 1) instead of pyridin-4-ylboronic acid. The resulting coupling product is then deprotected by the method described in Example 331 to give the title compound. LCMS: 410.1 m/z (M+H)+; ret. Time: 7.64 min. (Analytical Method C).

Workup

  1. customThe title compound was prepared similarly to the methods

Sources & evidence

ORD record
ord-db47c506ceaf4b42af6c3c5dd3fbb2ea
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

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