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Reaction Detail View in SciFinder n

Steps: 1

Yield: 81%

81%

Supplier (1)

Reference Company/Organization
(4+3) Annulation of Donor-Acceptor Cyclopr opanes and Laboratory of Catalysis and Organic Synthesis
Azadienes: Highly Stereoselective Synthesis of Azepanones
Institute of Chemical Sciences and Engineering
By: Nicolai, Stefano; Waser, Jerome Lausanne 1015
Switzerland
Angewandte Chemie, International Edition (2022), 61(36),
e202209006.

10.1002/anie.202209006
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Step 1

Alternative Steps (1)

CAS Reaction Number: 31-614-CAS-33649569

Stage Reagents Catalysts Solvents Conditions

1 Potassium carbonate - Methanol 4.5 h, 25 °C

Experimental Protocols

Synthetic Methods

Products 3-[[4-(1,1-Dimethylethyl)phenyl]methyl]-5-methyl-2,4(1H,3H)-pyrimidinedione, Yield: 81%

Reactants 1,1-Dimethylethyl 3-[[4-(1,1-dimethylethyl)phenyl]methyl]-3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-

pyrimidinecarboxylate

Reagents Potassium carbonate

Solvents Methanol

Procedure 1. Suspend tert-butyl 3- (4- (tert-butyl) benzyl) -5-methyl-2, 4-dioxo-3, 4-dihydropyrimidine-1 (2H) -
carboxylate (1.22 g, 3.28 mmol, 1.0 equiv.) in methanol (33 mL) in a 100 mL, single-necked, round-
bottomed flask.
2. Add K 2CO3 (0.453 g, 3.28 mmol, 1.0 equiv.) in a single portion.
3. Stir the resulting suspension vigorously at room temperature for 4.5 hours.
4. Add water (50 mL) and extract the resulting aqueous solution with DCM (4 x 50 mL).
5. Wash the combined organic layers once with sat. aq.NH 4Cl (50 mL), brine.
6. Dry over K 2CO3, filter and concentrate under vacuum.

Transformation Hydrolysis or Hydrogenolysis of Amides/ Imides/ Carbamates

Scale gram

Characterization Data

3-[[4-(1,1-Dimethylethyl)phenyl]methyl]-5-methyl-2,4(1 H,3H)-pyrimidinedione

Proton (400 MHz, Chloroform-d) δ 9.58 (s, 1H, Thymine-NH), 7.45 - 7.37 (m, 2H, ArH), 7.37 - 7.29 (m, 2H, ArH), 6.99 (dq,
NMR J =5.6, 1.3 Hz, 1H, Thymine-H), 5.09 (s, 2H, CH2Ar), 1.92 (d, J = 1.3 Hz, 3H, Thymine-Me), 1.29 (s, 9H, Ar-tBu)
Spectrum

State white solid

CAS Method Number 3-353-CAS-34969339

Copyright © 2023 American Chemical Society (ACS). All Rights Reserved.

Internal use only. Redistribution is subject to the terms of your SciFinderⁿ License Agreement and CAS information Use Policies.