Water → HCID 22125158, compound

HRID 1858255Notes

Reaction equation

HRID 1858255 reaction equation
[CH:1]([C:3]1[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][OH:20])[CH:13]=2)=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1)=O.[Br:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH2:24].O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1(C)C=CC=CC=1.O1CCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH:24][CH2:1][C:3]1[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][OH:20])[CH:13]=2)=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1

Participants

8

Reactant 4

HCID 962WaterHCID 119922-BromoanilineHCID 21226445Aluminium lithium hydrideHCID 22125006HCID 22125006, compound

Product 1

HCID 22125158HCID 22125158, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.5 g (8.65 mmol) of 5-formyl-4-[3-(2-hydroxyethyl)phenyl]amino-2-methylthiopyrimidine in 120 ml of toluene was treated with 1.5 g (9.3 mmol) of 2-bromoaniline and 100 mg (0.5 mmol) of 4-toluenesulfonic acid monohydrate and then heated at reflux with azeotropic removal of water for 1 hour. The cooled mixture was evaporated and the residue was dissolved in 4 ml of tetrahydrofuran. The solution obtained was added dropwise to a solution of 9 ml (9 mmol) of lithium aluminium hydride (as a 1M solution in tetrahydrofuran) in 40 ml of tetrahydrofuran. After 1 hour the reaction was quenched by the cautious dropwise addition of 0.35 ml of water, 0.35 ml of 2M aqueous sodium hydroxide and 1 ml of water. The resulting suspension was filtered through a filter aid and the filtrate was evaporated. The residue was partitioned between 150 ml of ethyl acetate and 50 ml of saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 3.5 g (91%) of 5-(2-bromoanilino)methyl-4-[3-(2-hydroxyethyl)phenyl]amino-2-methylthiopyrimidine as an orange colored gum. [Mass spectrum (ESI) MH+ =444].

Workup

  1. temperatureheated
  2. customThe cooled mixture was evaporated
  3. dissolutionthe residue was dissolved in 4 ml of tetrahydrofuran
  4. customThe solution obtained
  5. customAfter 1 hour the reaction was quenched by the cautious dropwise addition of 0.35 ml of water, 0.35 ml of 2M aqueous sodium hydroxide and 1 ml of water
  6. filtrationThe resulting suspension was filtered through a filter aid
  7. customthe filtrate was evaporated
  8. customThe residue was partitioned between 150 ml of ethyl acetate and 50 ml of saturated aqueous sodium bicarbonate solution
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-da24c2245fba44e1b0992c972d122805
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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