3,4-dihydro-2H-pyran → HCID 22125057, compound

HRID 1858268Notes

Reaction equation

HRID 1858268 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[NH:4][CH2:5][C:6]1[C:7]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][OH:23])[CH:16]=2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1.ClC1C=CC=C(Cl)C=1NCC1C(NC2C=[CH:46][CH:45]=[C:44]([CH2:48][CH2:49][OH:50])C=2)=NC(SC)=NC=1.BrC1C=CC=CC=1N.O1C=CCCC1>ClCCl.[Cl-].[Na+].O.O.C1(C)C(S(O)(=O)=O)=CC=CC=1.C(OCC)C>[Br:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[NH:4][CH2:5][C:6]1[C:7]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][O:23][CH:49]3[CH2:48][CH2:44][CH2:45][CH2:46][O:50]3)[CH:16]=2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1

Participants

9

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 119922-BromoanilineHCID 22125011HCID 22125011, compoundHCID 22125158HCID 22125158, compound

Product 1

HCID 22125057HCID 22125057, compound

Reagents, catalysts & solvents 4

HCID 124969952-Methylbenzenesulfonic acid hydrateCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 3.5 g (7.9 mmol) of 5-(2-bromoanilino)methyl-4-[3-(2-hydroxyethyl)phenyl]amino-2-methylthiopyrimidine (prepared in a method analogous to that for 5-(2,6-dichloroanilino)methyl-4-[3-(2-hydroxyethyl)phenyl]amino-2-methylthiopyrimidine of Example 37(f) using 2-bromoaniline in place of 2,6-dichloroaniline) in 100 ml of dichloromethane was treated with 3.3 g (39 mmol) of 2,3-dihydropyran and 15 mg (0.08 mmol) of toluenesulfonic acid monohydrate and the mixture stirred at room temperature for 3 days. Subsequently 100 ml of diethyl ether and 100 ml of brine were added. The mixture was separated and the organic phase dried over magnesium sulfate, filtered and evaporated. Flash chromatography on silica gel using diethyl ether and hexane in a ratio of 1:1 as eluent afforded 2.6 g of 5-(2-bromoanilino)methyl-4-[3-(2-(tetrahydropyranyloxy)ethyl)phenyl]amino-2-methylthiopyrimidine as a yellow oil. [Mass spectrum (ESI) MH+ =529].

Workup

  1. customThe mixture was separated
  2. dry with materialthe organic phase dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-66e4d63772c74a6386e4f5c5e5bdb83d
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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