Hydrochloric Acid → HCID 46200197, compound

HRID 1930540Notes

Reaction equation

HRID 1930540 reaction equation
Cl.[CH2:2]([NH:9][C:10]1[C:11]2[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][C:12]=2[N:13]=[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[O:27][CH:26]=[N:25][CH:24]=3)=[CH:19][CH:18]=2)[N:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[CH2:2]([NH:9][C:10]1[C:11]2[CH2:31][CH2:30][NH:29][CH2:28][C:12]=2[N:13]=[C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[O:27][CH:26]=[N:25][CH:24]=3)=[CH:21][CH:22]=2)[N:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59333754HCID 59333754, compound

Product 1

HCID 46200197HCID 46200197, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
76 °C

Procedure

Hydrogen chloride (2 mL, 0.20 mmol, 2M aq) was added to a solution of tert-butyl 4-(benzylamino)-2-(4-(oxazol-5-yl)phenylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (0.1 g, 0.20 mmol, Example 5a) in MeOH (5 mL) and heated in an open reaction vessel to 76° C. for 1 h. The residual solvent was removed under reduced pressure, the crude product was redissolved in DMSO and purified by preparative HPLC to give N4-benzyl-N2-(4-(oxazol-5-yl)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-2,4-diamine (38 mg, 47.5%). MS (ESI+)/(ESI−) m/z 399/397

Workup

  1. customThe residual solvent was removed under reduced pressure
  2. dissolutionthe crude product was redissolved in DMSO
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-bb392d0e0f6e41b994098021e3563c63
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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