Water → ethyl 5-chloro-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylate

HRID 869713Notes

Reaction equation

HRID 869713 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:11]=[C:4]2[N:3]=1.[NH2:17][CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(N(CC)CC)C.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:5]2[N:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:11]=[C:4]2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 4192234-AminotetrahydropyranHCID 86674517Ethyl 5,7-dichloropyrazolo[1,5-a]pyrimidine-2-carboxylate

Product 1

HCID 86674518ethyl 5-chloro-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 5,7-dichloropyrazolo[1,5-a]pyrimidine-2-carboxylate (7.82 g, 30.1 mmol) in N,N-dimethylformamide (100 mL) was added 4-amino-tetrahydropyran (3.65 g, 36.1 mmol) and triethylamine (9.12 g, 90.2 mmol) at 0° C. The reaction mixture was stirred for 70 min at room temperature, and then pored into water. The resulting precipitate was collected to give ethyl 5-chloro-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylate. MS (APCI): m/z 325 (M+H).

Workup

  1. customThe resulting precipitate was collected

Sources & evidence

ORD record
ord-9b1773a4de2a42a29ae43aab799aeba9
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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