Di-tert-butyl dicarbonate → HCID 118598567, compound

HRID 1050356Notes

Reaction equation

HRID 1050356 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15]C(C3CC3)=O)[CH:10]=2)[C:5](=[O:21])[N:4]2[C:22]([C:27]3[CH:32]=C[CH:30]=[C:29](F)[CH:28]=3)([CH3:26])[NH:23][C:24](=[O:25])[C:3]=12.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>O1CCCC1.CN(C)C1C=CN=CC=1>[NH2:15][C:11]1[N:12]=[CH:13][N:14]=[C:9]([NH:8][C:6]2[C:5](=[O:21])[N:4]3[C:22]([CH:27]4[CH2:32][CH2:30][CH2:29][CH2:28]4)([CH3:26])[NH:23][C:24](=[O:25])[C:3]3=[CH:2][CH:7]=2)[CH:10]=1

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 118598561HCID 118598561, compound

Product 1

HCID 118598567HCID 118598567, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5,6-dichloropyrimidin-4-amine (1, 3.0 g, 18.29 mmol) in tetrahydrofuran (30 mL), 4-dimethylaminopyridine (0.16 g, 1.31 mmol) and di-tert-butyl dicarbonate (8.77 g, 40.2 mmol) were added at room temperature. The reaction mass was stirred at room temperature for overnight. After completion, distilled out the solvent. The above residue was diluted with water and extracted with ethyl acetate (2×50 mL). The organics were then separated and dried (magnesium sulfate) and concentrated to dryness under vacuum to afford ethyl tert-butyl N-tert-butoxycarbonyl-N-(5,6-dichloropyrimidin-4-yl)carbamate (2) as white solid. Yield: 3.1 g, 47%; MS (ESI) m/z 364.3 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 9.04 (s, 1H), 1.40 (s, 18H).

Workup

  1. distillationAfter completion, distilled out the solvent
  2. additionThe above residue was diluted with water
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. customThe organics were then separated
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-5e9f280e0c204e3996bfe74a6feaffc8
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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