Acetone → 4-(2-chloro-6-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine

HRID 1626665Notes

Reaction equation

HRID 1626665 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[N:10]=[C:11]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:12]2[CH2:17][NH:16][CH2:15][C:13]=2[N:14]=1.Cl.[CH3:25][C:26]([CH3:28])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C(O)(=O)C>[Cl:8][C:9]1[N:10]=[C:11]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[C:12]2[CH2:17][N:16]([CH:26]([CH3:28])[CH3:25])[CH2:15][C:13]=2[N:14]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 866631634-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine trifluoroacetate2×

Product 1

HCID 866631744-(2-chloro-6-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine (intermediate 20) as a HCl salt (455 mg, 1.6 mmol) in anhydrous THF (5 ml) was added anhydrous acetone (500 μl) and glacial acetic acid (two drops). The reaction was stirred at RT for 30 minutes after which time sodium triacetoxyborohydride (696 mg, 3.3 mmol) was added. After stirring for a further 2 hours at RT the reaction was partitioned between water and DCM. The aqueous phase was extracted into DCM and the organic extracts were combined and concentrated in vacuo to afford the title compound as a brown oil which was used without further purification.

Workup

  1. additionwas added
  2. customwas partitioned between water and DCM
  3. extractionThe aqueous phase was extracted into DCM
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c325b0a2df74b9b95fadd320f4e36be
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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