Acetone → HCID 67817502, compound

HRID 1054524Notes

Reaction equation

HRID 1054524 reaction equation
[NH2:1][CH2:2][C@@H:3]1[C@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@H:6]2[C@H:5]([N:13]2[C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][CH:23]4[CH2:25][CH2:24]4)[C:16]=3[CH:15]=[CH:14]2)[CH2:4]1.[CH3:26][C:27](=O)[CH3:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:12][C:9]1([CH3:11])[O:8][C@@H:7]2[C@@H:3]([CH2:2][NH:1][CH:27]([CH3:28])[CH3:26])[CH2:4][C@@H:5]([N:13]3[C:17]4[N:18]=[CH:19][N:20]=[C:21]([NH:22][CH:23]5[CH2:25][CH2:24]5)[C:16]=4[CH:15]=[CH:14]3)[C@@H:6]2[O:10]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 67816524HCID 67816524, compound

Product 1

HCID 67817502HCID 67817502, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

7-[(3aS,4R,6R,6aR)-6-(Aminomethyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-N-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (1.900 g, 5.53 mmol) was dissolved in DCE (65 ml) and propan-2-one (0.81 ml, 11.1 mmol) was added and the reaction left for 15 mins. Sodium triacetoxyborohydride (1.642 g, 7.75 mmol) was added and the reaction left overnight. The reaction was quenched by the addition of sat. Na2CO3 solution (65 ml) and DCM (65 ml). The organic layer was separated and the aqueous layer was extracted with DCM (3×65 ml). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product. The product was purified by silica flash column chromatography using between 100% DCM and 20% 2M NH3 in MeOH:80% DCM as eluent to give the product as a pale yellow foamy solid (2.125 g, 100%): MS (ESI+) for C21H31N5O2 m/z 386.5 [M+H]+, 408.1 [M+Na]+; LC purity 100% (UV), 100% (ELS) (ret. time, 0.99 min); 1H NMR (500 MHz, CDCl3) δ 8.16 (s, 1H), 7.25 (d, J=3.63 Hz, 1H), 6.70 (br. s., 1H), 5.03 (dt, J=11.90, 6.19 Hz, 1H), 4.91-4.99 (m, 1H), 4.50-4.60 (m, 1H), 2.88 (quin, J=6.27 Hz, 2H), 2.78-2.85 (m, 1H), 2.70-2.78 (m, 1H), 2.38-2.46 (m, 1H), 2.35 (dt, J=12.37, 6.27 Hz, 1H), 2.06 (q, J=11.93 Hz, 1H), 1.55 (s, 3H), 1.31 (s, 3H), 1.11 (t, J=5.83 Hz, 6H), 0.81-0.96 (m, 2H), 0.55-0.72 (m, 2H).

Workup

  1. waitthe reaction left overnight
  2. customThe reaction was quenched by the addition of sat. Na2CO3 solution (65 ml) and DCM (65 ml)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with DCM (3×65 ml)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude product
  9. customThe product was purified by silica flash column chromatography

Sources & evidence

ORD record
ord-1f01eb4f09ba4dbe88b2be010e214a81
Source dataset
uspto-grants-2016_07
Patent number
US09394310B2

Reaction notes

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