Hydrochloric Acid → N2-(4-(2-Methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydro-2H-pyran-4-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

HRID 1930661Notes

Reaction equation

HRID 1930661 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[C:16]([NH:31][CH2:32][CH:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[C:17]4[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20][C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.Cl>CO>[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[C:16]([NH:31][CH2:32][CH:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[C:17]4[CH2:23][NH:22][CH2:21][CH2:20][C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59333695tert-Butyl 2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-4-((tetrahydro-2H-pyran-4-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Product 1

HCID 59333815N2-(4-(2-Methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydro-2H-pyran-4-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl 2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-4-((tetrahydro-2H-pyran-4-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (62 mg, 0.12 mmol) was dissolved in methanol (3 mL). Hydrochloric acid (3.63 μL, 0.12 mmol) was added and the reaction mixture was stirred at 80° C. for 1 h. The solvent was evaporated under reduced pressure and the crude N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-N4-((tetrahydro-2H-pyran-4-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (49.0 mg, 98%) was used as such in the subsequent step. MS (ES+) m/z 420.3 (M+H)+

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7559de3d2f924c738d6f6d16817b3089
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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