Hydrochloric Acid → HCID 57695464, compound

HRID 1517357Notes

Reaction equation

HRID 1517357 reaction equation
[O:1]=[C:2]1[N:7]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C@H:15]([NH:19]C(=O)OC(C)(C)C)[CH2:16][C:17]#[CH:18])=[N:5][C:4]2[CH:27]=[CH:28][CH:29]=[N:30][C:3]1=2.Cl>CO>[NH2:19][C@@H:15]([C:6]1[N:7]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:2](=[O:1])[C:3]2[N:30]=[CH:29][CH:28]=[CH:27][C:4]=2[N:5]=1)[CH2:16][C:17]#[CH:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57695426HCID 57695426, compound

Product 1

HCID 57695464HCID 57695464, compoundYield 121.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 1-(4-oxo-3-(phenylamino)-3,4-dihydropyrido[3,2-d]pyrimidin-2-yl)but-3-ynylcarbamate (1.20 g, 2.96 mmol) in methanol (15 ml) was added 4.5 ml of HCl (4.0 M in 1,4-dioxane). The reaction was carried out at room temperature for 18 hours. The solvent was removed under reduced pressure to afford (R)-2-(1-aminobut-3-ynyl)-3-(phenylamino)pyrido[3,2-d]pyrimidin-4(3H)-one (1.1 g) as a light brown solid, M.p. 206-208° C. LCMS: m/e 306 [M+H]. 1H NMR (400 MHz) (DMSO-d6): δ 9.34 (s, 1H), 8.85 (s, 1H), 8.20 (d, J=8 Hz, 1H), 7.94 (dd, J=8.0 Hz and 3.2 Hz, 1H), 7.22 (t, J=7.6 Hz, 2H), 6.91 (t, J=7.6 Hz, 1H), 6.80 (s, J=8 Hz, 1H), 4.98 (m, 3H), 4.53 (s, 1H), 3.11 (m, 2H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0f4f47d1f9344efa8f73e5515e6ec06a
Source dataset
uspto-grants-2012_07
Patent number
US08232285B2

Reaction notes

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