P-Anisidine → HCID 178492151, compound

HRID 1243189Notes

Reaction equation

[C:1]([Si:5]([CH3:34])([CH3:33])[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:18]3=[N:19][C:20](Cl)=[N:21][CH:22]=[C:17]3[CH2:16][N:15]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:14]2=[O:32])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[CH3:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([NH2:43])=[CH:39][CH:38]=1>CC(O)C>[C:1]([Si:5]([CH3:34])([CH3:33])[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:18]3=[N:19][C:20]([NH:43][C:40]4[CH:41]=[CH:42][C:37]([O:36][CH3:35])=[CH:38][CH:39]=4)=[N:21][CH:22]=[C:17]3[CH2:16][N:15]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:14]2=[O:32])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 1-[trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-7-chloro-3-(4-methoxy-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (0.20 g, 0.40 mmol) (from Example 19a supra) and p-anisidine (63.6 mg, 0.52 mmol) (Aldrich) in 2-propanol (4 mL) was placed in a microwave reactor (SmithSynthesizer™). The reaction mixture was heated at 160° C. for 10 minutes. After cooling, it was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate-hexanes (3:7 then 2:3) to give 1-[trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-3-(4-methoxy-phenyl)-7-(4-methoxy-phenylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one. (Yield 0.14 g, 58%).

Workup

customwas placed in a microwave reactor
temperatureAfter cooling
concentrationit was concentrated under reduced pressure
customThe residue was purified by flash chromatography
washeluting with ethyl acetate-hexanes (3:7

Sources & evidence

ORD record: ord-760334091dad4ed1bd061e6397b0a116
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115740B2

Reaction notes

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