Formaldehyde → HCID 67818815, compound

HRID 1054553Notes

Reaction equation

HRID 1054553 reaction equation
[Cl:1][C:2]1[C:47]([Cl:48])=[CH:46][C:5]2[N:6]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][C@@H:15]3[C@H:19]4[O:20][C:21]([CH3:24])([CH3:23])[O:22][C@H:18]4[C@H:17]([N:25]4[C:29]5[N:30]=[CH:31][N:32]=[C:33]([NH:34][CH:35]6[CH2:37][CH2:36]6)[C:28]=5[CH:27]=[CH:26]4)[CH2:16]3)=[N:8][C:4]=2[CH:3]=1.CO.C=O.[BH3-][C:54]#N.[Na+]>C1COCC1>[Cl:1][C:2]1[C:47]([Cl:48])=[CH:46][C:5]2[N:6]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:43])([CH3:44])[CH3:45])[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:14][C@@H:15]3[C@H:19]4[O:20][C:21]([CH3:24])([CH3:23])[O:22][C@H:18]4[C@H:17]([N:25]4[C:29]5[N:30]=[CH:31][N:32]=[C:33]([NH:34][CH:35]6[CH2:36][CH2:37]6)[C:28]=5[CH:27]=[CH:26]4)[CH2:16]3)[CH3:54])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 67818137HCID 67818137, compound

Product 1

HCID 67818815HCID 67818815, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-[(3aS,4R,6R,6aR)-6-({[4-(5,6-Dichloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)butyl]amino}methyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-N-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.222 g, 0.311 mmol) was dissolved in THF (5 ml) and MeOH (5 ml) and formaldehyde (0.05 ml, 0.621 mmol) was added at r.t. under N2. NaBH3CN (0.023 g, 0.373 mmol) was added at r.t. and the reaction left for 2 hrs. After this time LCMS analysis showed the reaction was complete so the reaction was quenched by addition of sat. NaHCO3 solution (10 ml), water (10 ml) and DCM (10 ml). The organic layer was separated and the aqueous layer was extracted with DCM (2×10 ml). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product. The crude product was purified by silica flash column chromatography using between 100% DCM and 15% MeOH:95% DCM as eluent to give the product as a colorless oil

Workup

  1. customwas quenched by addition of sat. NaHCO3 solution (10 ml), water (10 ml) and DCM (10 ml)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (2×10 ml)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product
  8. customThe crude product was purified by silica flash column chromatography

Sources & evidence

ORD record
ord-608e19ded3a84de0883f4e81a4470d97
Source dataset
uspto-grants-2016_07
Patent number
US09394310B2

Reaction notes

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