tert-Butyl 3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)azetane-1-carboxylate → 1-(azetidin-3-y)-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 516148Notes

Reaction equation

HRID 516148 reaction equation
NC1N=CN=C2N(C3CN(C(OC(C)(C)C)=O)C3)N=C(I)C=12.[NH2:23][C:24]1[N:29]=[CH:28][N:27]=[C:26]2[N:30]([CH:45]3[CH2:49]C[N:47](C(OC(C)(C)C)=O)[CH2:46]3)[N:31]=[C:32]([C:33]#[C:34][C:35]3[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[C:37]([O:43][CH3:44])[CH:36]=3)[C:25]=12>>[NH:47]1[CH2:46][CH:45]([N:30]2[C:26]3=[N:27][CH:28]=[N:29][C:24]([NH2:23])=[C:25]3[C:32]([C:33]#[C:34][C:35]3[CH:36]=[C:37]([O:43][CH3:44])[CH:38]=[C:39]([O:41][CH3:42])[CH:40]=3)=[N:31]2)[CH2:49]1

Participants

3

Reactant 2

HCID 22346992tert-Butyl 3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)azetane-1-carboxylateHCID 89870803tert-butyl 3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidine-1-carboxylate

Product 1

HCID 898710651-(azetidin-3-y)-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Procedure

In accordance with Example 1 (Step 4), except that tert-butyl 3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)azetidine-1-carboxylate obtained in Step 3 above was used in place of tert-butyl 3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidine-1-carboxylate, a crude product of 1-(azetidin-3-yl)-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine was obtained by removing a Boc group under acidic conditions. Thereafter, amidation was conducted to obtain the title compound as a white solid. Table 1 shows the physical properties thereof.

Sources & evidence

ORD record
ord-9ccc7680a987458f827ba54ddd291945
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

Loading…