Acetic Anhydride → HCID 58169226, compound

HRID 1484954Notes

Reaction equation

HRID 1484954 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[C:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][N:3]=1.[CH3:22][C:23](OC(C)=O)=[O:24]>C1COCC1.O>[C:23]([N:11]1[C:12]([CH:14]2[CH2:15][CH2:16]2)=[CH:13][C:9]([NH:8][C:6]2[C:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][N:3]=[C:2]([Br:1])[N:7]=2)=[N:10]1)(=[O:24])[CH3:22]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 58169573HCID 58169573, compound

Product 1

HCID 58169226HCID 58169226, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To the mixture of ethyl 2-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-5-carboxylate (495 mg, 1.41 mmol) in THF (100 mL) and water (10 mL) was added Ac2O (2.0 mL). The reaction mixture was stirred for 2 h and water was added. The mixture was filtered and the solid was washed with water and concentrated with ethanol to remove the residual water to obtain ethyl 4-(1-acetyl-5-cyclopropyl-1H-pyrazol-3-ylamino)-2-bromopyrimidine-5-carboxylate (460 mg, 83%). LC-MS (m/z)=394.0 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with water
  3. concentrationconcentrated with ethanol
  4. customto remove the residual water

Sources & evidence

ORD record
ord-55c36c5dfc3447e0925f8aeb00bd941e
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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