5-Ethynylpyridin-2-amine → [3-(6-Amino-pyridin-3-ylethynyl)-5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-methanol

HRID 1294024Notes

Reaction equation

HRID 1294024 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH2:14][OH:15])[N:11]3[N:16]=[CH:17][C:18](I)=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:20]([C:22]1[CH:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=1)#[CH:21]>>[NH2:28][C:25]1[N:26]=[CH:27][C:22]([C:20]#[C:21][C:18]2[CH:17]=[N:16][N:11]3[C:12]([CH2:14][OH:15])=[CH:13][C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)=[N:9][C:10]=23)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 219548275-Ethynylpyridin-2-amineHCID 67001059[5-(4-Chloro-phenyl)-3-iodo-pyrazolo[1,5-a]pyrimidin-7-yl]-methanol

Product 1

HCID 67001053[3-(6-Amino-pyridin-3-ylethynyl)-5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-methanol

Procedure

The title compound was prepared from [5-(4-chloro-phenyl)-3-iodo-pyrazolo[1,5-a]pyrimidin-7-yl]-methanol (example C.14 step 2) (193 mg, 0.5 mmol) and 5-ethynyl-pyridin-2-ylamine (example D.1) (59 mg, 0.5 mmol) according to general procedure II. Obtained as an orange solid (111 mg, 59%). MS (ISP) 376.4 [(M+H)+]; mp 215–217° C.

Sources & evidence

ORD record
ord-15f773de53c44233bdd322721ed1c87c
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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