2,4-Dichloroaniline → HCID 22125143, compound

HRID 1858298Notes

Reaction equation

C([CH:5]([O:34][SiH](C1C=CC=CC=1)C1C=CC=CC=1)[CH2:6][C:7]1[CH:8]=[C:9]([N:13]2[C:18]3=[N:19][C:20]([S:23][CH3:24])=[N:21][CH:22]=[C:17]3[CH2:16][N:15]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=3[Cl:32])[C:14]2=[O:33])[CH:10]=[CH:11][CH:12]=1)(C)(C)C.ClC1C=C(Cl)C=CC=1N.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[Cl:32][C:26]1[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:25]=1[N:15]1[CH2:16][C:17]2[C:18](=[N:19][C:20]([S:23][CH3:24])=[N:21][CH:22]=2)[N:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][CH2:5][OH:34])[CH:8]=2)[C:14]1=[O:33]

Participants

Reactant 3

HCID 111232,4-Dichloroaniline

HCID 2724141Tetrabutylammonium Fluoride

HCID 137329274HCID 137329274, compound

Product 1

HCID 22125143HCID 22125143, compoundYield 100%

Procedure

1.97 g (2.83 mmol) of 1-[3-(2-tertbutyldiphenylsilyloxyethyl)phenyl]-3-(2,4-dichlorophenyl)-3,4-dihydro-7-methylthio-pyrimido[4,5-d]pyrimidin-2(1H)-one (prepared in a manner analogous to that described in Example 53(a)-(b) using 2,4-dichloroaniline in place of 2-chloro-6-methylaniline) was reacted with a 1M solution of tetrabutylammonium fluoride in a manner analogous to that described in Example 69. 1.3 g (100%) of 3-(2,4-dichlorophenyl)-3,4-dihydro-1-[3-(2-hydroxyethyl)phenyl]-7-methylthio-pyrimido[4,5-d]pyrimidin-2(1H)-one was isolated as a yellow solid. [Mass spectrum (ESI) MH+ =461].

Sources & evidence

ORD record: ord-8cc854d3b2f64d5b8f5d46fcea70979b
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150373

Reaction notes

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