Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate → HCID 69669156, compound

HRID 450579Notes

Reaction equation

HRID 450579 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.Cl[C:24]1[C:25]2[C:32]([CH3:33])=[C:31]([C:34]([O:36][CH3:37])=[O:35])[S:30][C:26]=2[N:27]=[CH:28][N:29]=1.O.[OH-].[NH4+]>O1CCOCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][CH:5]([O:4][C:3]2[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:2]=2[NH:1][C:24]2[C:25]3[C:32]([CH3:33])=[C:31]([C:34]([O:36][CH3:37])=[O:35])[S:30][C:26]=3[N:27]=[CH:28][N:29]=2)[CH2:6][CH2:7]1)=[O:12])([CH3:16])([CH3:17])[CH3:15]

Participants

7

Reactant 3

HCID 2759834Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylateHCID 69669353HCID 69669353, compoundHCID 86589665Water ammonium hydroxide

Product 1

HCID 69669156HCID 69669156, compoundYield 65.7%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-(2-amino-5-fluorophenoxy)piperidine-1-carboxylate (0.865 g, 2.8 mmol), methyl 4-chloro-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (0.675 g, 2.8 mmol) and para-toluene sulfonic acid (0.026 g, 0.14 mmol) were heated at 90° C. in anhydrous 1,4-dioxane (8 mL) for 1.5 hours. The solution was cooled to ambient temperature, diluted with water (2 mL) and adjusted to pH 10 (4:1 water/ammonium hydroxide solution). The precipitate was collected, washed with water and diethyl ether to yield the title compound as yellow solid (0.95 g, 65%).

Workup

  1. customThe precipitate was collected
  2. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-7a06a8853853445cae6e1ced9a448c21
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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