Methanol → HCID 68433138, compound

HRID 1162849Notes

Reaction equation

HRID 1162849 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[N:16]2[C:17](=[O:26])[N:18]([CH:23]([CH3:25])[CH3:24])[C:19](=[O:22])[C:20]([OH:21])=[C:15]2[C:14](=[O:27])[N:13]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:45][C:46]([CH3:51])([CH3:50])[C:47](Cl)=[O:48].CO>ClCCl>[C:47]([O:21][C:20]1[C:19](=[O:22])[N:18]([CH:23]([CH3:25])[CH3:24])[C:17](=[O:26])[N:16]2[CH:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:12][N:13]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[C:14](=[O:27])[C:15]=12)(=[O:48])[C:46]([CH3:51])([CH3:50])[CH3:45]

Participants

6

Reactant 4

HCID 887MethanolHCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 54692321HCID 54692321, compound

Product 1

HCID 68433138HCID 68433138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[2-(benzyloxy)ethyl]-2-(4-fluorobenzyl)-9-hydroxy-7-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione (Example 9, Step 6, 1.18 g, 2.46 mmol) in anhydrous dichloromethane (20 mL) at 0° C. were added diisopropylethylamine (856 μL, 4.91 mmol), trimethylacetyl chloride (454 μL, 3.69 mmol), and N,N-dimethylaminopyridine (60 mg, 0.49 mmol). The mixture was stirred at ambient temperature under inert atmosphere for 1.5 h. Addition of methanol resulted in the precipitation of the title compound as a white solid. 1H NMR (CDCl3, 400 MHz): δ 7.39-7.26 (m, 5 H), 7.07-7.03 (m, 2 H), 6.97-6.93 (m, 2 H), 5.18-5.12 (m, 1 H), 4.79 (m, 1 ), 4.64-4.58 (m, 1 H), 4.47-4.34 (m, 3 H), 3.66-3.54 (m, 1 H), 3.45-3.27 (m, 3 H), 1.88 (m, 1 H), 1.77-1.72 (m, 1 H), 1.46-1.44 (m, 6 H), 1.40 (s, 9 H). ES MS (M+1)=566.7.

Sources & evidence

ORD record
ord-e125981fb4a142fea66557f558dbd7c7
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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