Chlorotrimethylsilane → 6-(2-(1H-indazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 645698Notes

Reaction equation

HRID 645698 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:24]=[CH:23][C:15]3[O:16][C:17]([CH3:22])([CH3:21])[C:18](=[O:20])[NH:19][C:14]=3[CH:13]=2)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[NH2:25][C:26]1[CH:34]=[C:33]2[C:29]([CH:30]=[N:31][NH:32]2)=[CH:28][CH:27]=1.C[Si](Cl)(C)C>C(O)CCC>[NH:32]1[C:33]2[C:29](=[CH:28][CH:27]=[C:26]([NH:25][C:2]3[N:3]=[C:4]([NH:11][C:12]4[CH:24]=[CH:23][C:15]5[O:16][C:17]([CH3:22])([CH3:21])[C:18](=[O:20])[NH:19][C:14]=5[CH:13]=4)[C:5]4[CH:10]=[CH:9][NH:8][C:6]=4[N:7]=3)[CH:34]=2)[CH:30]=[N:31]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 814231H-Indazol-6-amineHCID 866280386-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 251960136-(2-(1H-indazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 6.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
115 °C

Procedure

To a mixture of 6-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.050 g) inn-butyl alcohol (0.6 mL) was added 6-aminoindazole (0.028 g) and trimethylsilyl chloride (TMSCl) (0.013 mL). After heating at 115° C. for 15 h, the mixture was purified by preparative HPLC to give 6-(2-(1H-indazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.004 g, MS [MH] 441.1) (Compound 16-1).

Workup

  1. customthe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-58013d8bb578455dbc65aaca5e1fd0e3
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

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