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

HRID 645697Notes

Reaction equation

HRID 645697 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.CCN(C(C)C)C(C)C.[NH2:21][C:22]1[CH:34]=[CH:33][C:25]2[O:26][C:27]([CH3:32])([CH3:31])[C:28](=[O:30])[NH:29][C:24]=2[CH:23]=1>CS(C)=O.C(OC(=O)C)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:34]=[CH:33][C:25]3[O:26][C:27]([CH3:31])([CH3:32])[C:28](=[O:30])[NH:29][C:24]=3[CH:23]=2)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 136654966-Amino-2,2-dimethyl-2H-benzo[B][1,4]oxazin-3(4H)-oneHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 866280386-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 48.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine (0.056 g, 0.30 mmol) in dimethylsulfoxide (1 mL) was added DIPEA (0.12 mL, 0.60 mmol) and 6-amino-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.085 g, 0.44 mmol). After heating at 100° C. for 15 h, the mixture was diluted with ethylacetate and sequentially washed with saturated NaHCO3 and brine. The organic extracts were dried over Na2SO4 and concentrated to give 6-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.05 g).

Workup

  1. washsequentially washed with saturated NaHCO3 and brine
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-96a8bb15fa954be489846074de0fe271
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

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