Water → (S)-2-(1-(6-amino-5-iodopyrimidin-4-ylamino)ethyl)-5-chloro-3-phenylquinazolin-4(3H)-one

HRID 1474074Notes

Reaction equation

[NH2:1][C@H:2]([C:4]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:12](=[O:20])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:21])[N:5]=1)[CH3:3].[NH2:22][C:23]1[C:28]([I:29])=[C:27](Cl)[N:26]=[CH:25][N:24]=1.CCN(C(C)C)C(C)C.O>CC(O)C>[NH2:22][C:23]1[N:24]=[CH:25][N:26]=[C:27]([NH:1][C@H:2]([C:4]2[N:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:12](=[O:20])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[Cl:21])[N:5]=2)[CH3:3])[C:28]=1[I:29]

Participants

Conditions

Temperature: 90 °C

Procedure

To (S)-2-(1-aminoethyl)-5-chloro-3-phenylquinazolin-4(3H)-one (400 mg, 1.33 mmol) (prepared according to the procedure in Example 2a.A above) and 4-amino-6-chloro-5-iodopyrimidine (338 mg, 1.32 mmol) in IPA (5 mL) was added Hunig's base (0.4 mL). After stirring at 90° C. for 2 hours in a microwave reactor, water was added and the mixture was extracted with EtOAc (3×50 mL), dried (MgSO4), and concentrated. The residue was purified on a reverse phase system run from 0 to 95% ACN in water (0.1% TFA) to give (S)-2-(1-(6-amino-5-iodopyrimidin-4-ylamino)ethyl)-5-chloro-3-phenylquinazolin-4(3H)-one. ES/MS m/z=519.0 (M+), 521.0 (M+2).

Workup

extractionthe mixture was extracted with EtOAc (3×50 mL)
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was purified on a reverse phase system

Sources & evidence

ORD record: ord-be891331a8554bcca565edcea9159ccd
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018221B2

Reaction notes

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