2-Butyne-1,4-diol → HCID 10233725, compound

HRID 2085108Notes

Reaction equation

HRID 2085108 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19](Cl)[N:18]=[C:17]([C:31]3[N:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:37][O:38][C:39]1[CH:40]=[C:41]([CH:49]=[CH:50][CH:51]=1)[CH2:42][O:43][CH2:44][C:45]#[C:46][CH2:47][OH:48].C(O)C#CCO.COC1C=C(C=CC=1)CBr>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([O:48][CH2:47][C:46]#[C:45][CH2:44][O:43][CH2:42][C:41]3[CH:49]=[CH:50][CH:51]=[C:39]([O:38][CH3:37])[CH:40]=3)[N:18]=[C:17]([C:31]3[N:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 80662-Butyne-1,4-diolHCID 40672073-Methoxybenzyl bromideHCID 111351604-Tert-butyl-n-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamideHCID 22729410HCID 22729410, compound

Product 1

HCID 10233725HCID 10233725, compoundYield 25.7%

Procedure

Crude 4-tert.-butyl-N-[6-(4-(3-methoxybenzyloxy)-2-butynyloxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide was obtained starting from 300 mg of 4-tert.-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide (Example 5a) and 1096 mg of 4-(3-methoxybenzyloxy)-2-butyn-1-ol (prepared starting from 2-butyn-1,4-diol and 3-methoxybenzylbromide in analogy to a procedure reported in Tetrahedron Lett. 38 (1997), 7887-7890) following the procedure given in Example 91. The compound was purified by column chromatography on silica gel eluting with DCM containing 0-2.5% of methanol followed by chromatography on prep. tlc-plates with DCM containing 5% of methanol. The resulting oil was dissolved in 10 ml of diethyl ether and treated with pentane. The precipitate was collected and dried to give 102 mg of 4-tert.-butyl-N-[6-(4-(3-methoxybenzyloxy)-2-butynyloxy)-5-(o-methoxy-phenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide as an almost white powder. LC-MS: tR=5.74 min, [M+1]+=696.40, [M−1]−=694.32.

Workup

  1. customprepared
  2. customThe compound was purified by column chromatography on silica gel eluting with DCM containing 0-2.5% of methanol
  3. dissolutionThe resulting oil was dissolved in 10 ml of diethyl ether
  4. additiontreated with pentane
  5. customThe precipitate was collected
  6. customdried

Sources & evidence

ORD record
ord-50f93010246c4bc593fb74e717e68fc5
Source dataset
uspto-grants-2004_04
Patent number
US06720322B2

Reaction notes

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