Cyanide → 4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine

HRID 1418773ノート

反応式

HRID 1418773 の反応式
[C:1]([C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].ClC1N=[CH:14][CH:13]=[CH:12][N:11]=1.[C-]#N.N12CCC(CC1)CC2.N12CCN(CC1)CC2.N.[NH4+].[Cl-:36].C[O-].[Na+].CO.[ClH:42].N1C=CC=NC=1C(N)=N.C[O-].[Na+].[CH3:55][O:56][C:57]1[CH:74]=[CH:73][CH:72]=[CH:71][C:58]=1[O:59]C(C(OCC)=O)C(OCC)=O.COC1C=CC=CC=1OC1C(=O)NC(C2N=CC=CN=2)NC1=O.C(N(C(C)C)CC)(C)C.P(Cl)(Cl)(Cl)(Cl)Cl>>[Cl:36][C:5]1[C:6]([O:59][C:58]2[CH:71]=[CH:72][CH:73]=[CH:74][C:57]=2[O:56][CH3:55])=[C:7]([Cl:42])[N:8]=[C:3]([C:1]2[N:11]=[CH:12][CH:13]=[CH:14][N:2]=2)[N:4]=1

参加物

14

反応物 13

HCID 5975CyanideHCID 7527QuinuclidineHCID 9237DabcoHCID 24819Phosphorus pentachlorideHCID 744042-ChloropyrimidineHCID 81531DiisopropylethylamineHCID 27579792-Cyanopyrimidine2 回HCID 10942334Sodium MethoxideHCID 11140560Diethyl (2-methoxyphenoxy)propanedioateHCID 219795675-(2-Methoxyphenoxy)-2-(pyrimidin-2-yl)-tetrahydropyrimidin-4,6-dioneHCID 219837312-Amidinopyrimidine hydrochlorideHCID 23694274Sodium methanolate methanolHCID 86743336Ammonia ammonium chloride

生成物 1

HCID 105457064,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine

実験手順

Another particularly useful process is for manufacturing 4-tert.butyl-N-6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-2-(pyrimidin-2-yl)-pyrimidin-4-yl-benzenesulphonamide, This process comprises manufacturing 2-cyanopyrimidine by reacting 2-chloropyrimidine with an alkali cyanide in the presence of 1-azabicyclo[2,2,2]octane or 1,4-diazabicyclo[2,2,2]octane. The 2-cyano pyrimidine is then converted by means of NH3 /NH4Cl in a sodium methanolate/methanol solution into pyrimidin-2-carboxamidine hydrochloride. The pyrimidine-2-caroboxamidine hydrochloride is then converted in the presence of sodium methanolate with diethyl (o-methoxy-phenoxy-malonate) into rac-5-(2-methoxy-phenoxy)-2-pyrimidin-2-yl-tetrahydro-pyrimidin-4,6-dione. This product is then reacted with N,N-diisopropyl-N-ethylamine and phosphorus pentachloride to give 4,6-dichloro-5-(2-methoxy-phenoxy)-2,2'-bipyrimidine. This in turn is reacted with p-tert.butylbenzenesulphonamide to give 4-tert.butyl-N-6-chloro-5-[2-(2-methoxy-phenoxy)-2-(pyrimidin-2-yl)-pyrimidin-4-yl]-benzenesulphonamide which is reacted with sodium ethylene glycolate to give 4-tert.butyl-N-6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-2-(pyrimidin-2-yl)-pyrimidin-4-yl-benzenesulphonamide.

出典と根拠

ORDレコード
ord-2542dc532644460fb7351c7a857fc078
出典データセット
uspto-grants-1999_03
特許番号
US05883254

反応ノート

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