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Ethyl chloroformate → (S)-ethyl 2-(4-(3-cyclopropylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 1626557
Notes
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Reaction equation

HRID 1626557 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]4[CH3:29])[C:17]4[CH2:22][NH:21][CH2:20][C:18]=4[N:19]=3)=[CH:10][CH:9]=2)=[O:6])[CH2:3][CH2:2]1.C(=O)([O-])O.[Na+].Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37]>O1CCOCC1>[CH:1]1([NH:4][C:5](=[O:6])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:15]=[C:16]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]4[CH3:29])[C:17]4[CH2:22][N:21]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:20][C:18]=4[N:19]=3)=[CH:12][CH:13]=2)[CH2:2][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 46894114(S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

Product 1

HCID 46912384(S)-ethyl 2-(4-(3-cyclopropylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Procedure

To a solution of (S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (example 3) (50 mg 0.13 mmol) in dioxane (3 mL) at room temperature (20° C.) was added sodium hydrogencarbonate (22 mg 0.26 mmol) followed by ethyl chloroformate (14 uL 0.15 mmol). The reaction mixture was stirred for 16 h. The solvent was removed in vacuo and the residue partitioned between DCM and water. The organic phase was passed through a 1 micron PTFE filter to dry and then evaporated in vacuo to afford (38 mg 64%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between DCM and water
  3. filtrationfilter
  4. customto dry
  5. customevaporated in vacuo
  6. customto afford (38 mg 64%)

Sources & evidence

ORD record
ord-7075027403cb4a1c8f4df49ab2b87a36
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785457B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes