HRID1066509

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.F[P-](F)(F)(F)(F)F

HCID151348

Tri(dimethylamino)benzotriazol-1-yloxyphosphonium hexafluorophosphate

C12H22F6N6OP2

结构：COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C)cn2)nc(-c2ccnc(C(=O)O)c2)nc1OC

HCID9892985

未命名化合物

2 次

PRODUCTS

生成物

结构：COC(=O)c1cc(-c2nc(NS(=O)(=O)c3ccc(C)cn3)c(Oc3ccccc3OC)c(OC)n2)ccn1

HCID9958841

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

220 mg of 4-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid, product of example 21, suspended in acetontrile (10 ml) was treated at RT subsequently with 27 mg of methanol, 100 mg of 4-(dimethylamino)pyridine (DMAP) and 186 mg of benzotriazol-1-yloxytris-(dimethylamino)-phosphonium hexafluorophosphate (BOP). The mixture was stirred for 12 h at RT, then partitioned between cold diluted HCl and EtOAc. The layers were separated, the organic layer dried over Na2SO4 and the solvent removed in vacuo. The residue was purified on a silica gel chromatography column (eluted with Me2Cl2/MeOHc: 95/5). Combination of the purified fractions and evacuation in vacuo afforded 4-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid methyl ester as a white solid. ISN mass spectrum, m/e 536.2 (M−1 calculated for C25H23N5O7S: 536).

WORKUP

后处理

custompartitioned between cold diluted HCl and EtOAc
customThe layers were separated
dry with materialthe organic layer dried over Na2SO4
customthe solvent removed in vacuo
customThe residue was purified on a silica gel chromatography column (eluted with Me2Cl2/MeOHc: 95/5)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d0b1af57755d4063a07e5d7a6ff88c8b
来源数据集: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06242601B1
来源说明: uspto-grants-2001_06

反应 SMILES

[CH3:1][O:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[C:7]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=2)(=[O:21])=[O:20])[N:6]=[C:5]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([C:35]([OH:37])=[O:36])[CH:30]=2)[N:4]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=C[C:48]=2N=N1>CN(C)C1C=CN=CC=1.CO>[CH3:48][O:36][C:35]([C:31]1[CH:30]=[C:29]([C:5]2[N:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][CH3:17])=[C:7]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=3)(=[O:21])=[O:20])[N:6]=2)[CH:34]=[CH:33][N:32]=1)=[O:37]