Ethyl Acetate → HCID 69643731, compound

HRID 1370074Notes

Reaction equation

HRID 1370074 reaction equation
[N+]([O-])([O-])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([NH:17][C:18]([NH2:20])=[NH2+:19])[CH:10]=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14].[C:21]([O:25][C:26]([NH:28][C:29]([C:32]1[CH:37]=[CH:36][C:35]([C:38](=O)[C:39]([C:44]#N)=[CH:40][N:41](C)C)=[CH:34][CH:33]=1)([CH3:31])[CH3:30])=[O:27])([CH3:24])([CH3:23])[CH3:22].[OH-].[Na+].C(OCC)(=O)C>CCCCCC>[NH2:28][C:29]([C:32]1[CH:33]=[CH:34][C:35]([C:38]2[C:39]([C:40]#[N:41])=[CH:44][N:20]=[C:18]([NH:17][C:9]3[CH:10]=[C:11]([O:15][CH3:16])[C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=3)[N:19]=2)=[CH:36][CH:37]=1)([CH3:31])[CH3:30].[C:21]([O:25][C:26]([NH:28][C:29]([C:32]1[CH:37]=[CH:36][C:35]([C:38]2[C:39]([C:40]#[N:41])=[CH:44][N:20]=[C:18]([NH:17][C:9]3[CH:10]=[C:11]([O:15][CH3:16])[C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=3)[N:19]=2)=[CH:34][CH:33]=1)([CH3:31])[CH3:30])=[O:27])([CH3:23])([CH3:22])[CH3:24]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 54158929HCID 54158929, compoundHCID 178419082HCID 178419082, compound

Product 2

HCID 18516875HCID 18516875, compoundHCID 69643731HCID 69643731, compoundYield 164.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The title compound was prepared from 3,4,5-trimethoxyphenylguanidinium nitrate (576 mg, 2.0 mmol), 1-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-2-cyano-3-dimethylaminopropen-1-one (660 mg, 1.8 mmol) and powdered sodium hydroxide (89 mg, 2.2 mmol) following the method described for the compound of Example 8. This gave the intermediate 4-[4-(1-tert-butoxycabonylamino-1methylethyl)phenyl]-5-cyano-N-(3,4,5-trimethoxyphenyl)pyrimidine-2-amine as a yellow solid (769 mg) after column chromatography (silica, 40% ethyl acetate in hexane). This compound was treated with TFA acid in CH2Cl2 as descibed for the analogous compound of Example 8 to give the title compound as a pale yellow solid (597 mg) m.p. 167-168°. δH (d6 DMSO) 10.34 (1H, bs), 8.90 (1H, s), 7.96 (2H, bd, J 7.8 Hz), 7.73 (2H, d, J 8.2 Hz), 7.24 (2H, bs), 3.76 (6H, s), 3.63 (3H, s), 3.18 (2H, bs), 1.42 (6H, s). MS (ESI) 442 (MNa+, 16%), 420 (MH+, 57%), 403 (100%).

Sources & evidence

ORD record
ord-da95fe2c3138444e9b59cf673fe4bfda
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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