Pyrimidine-5-carboxylic acid → HCID 178493856, compound

HRID 1259500Notes

Reaction equation

HRID 1259500 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([NH2:13])[N:9]3[CH2:14][CH2:15][N:16]=[C:8]3[C:7]=2[CH:6]=[CH:5][C:4]=1[O:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.[N:27]1[CH:32]=[C:31]([C:33](O)=[O:34])[CH:30]=[N:29][CH:28]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([NH:13][C:33]([C:31]3[CH:32]=[N:27][CH:28]=[N:29][CH:30]=3)=[O:34])[N:9]3[CH2:14][CH2:15][N:16]=[C:8]3[C:7]=2[CH:6]=[CH:5][C:4]=1[O:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1

Participants

7

Reactant 4

HCID 78346Pyrimidine-5-carboxylic acidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 178493860HCID 178493860, compound

Product 1

HCID 178493856HCID 178493856, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (100 mg, 0.22 mol) was dissolved in DMF (5 mL), and pyrimidine-5-carboxylic acid (41 mg, 0.33 mmol) was added. PYBOP (173 mg, 0.33 mmol) and diisopropylethylamine (0.16 mL, 0.89 mmol) were subsequently added, and the mixture was stirred at rt overnight. EtOAc was added, and the precipitate was isolated by vacuum filtration to give the title compound (12 mg, 11%): HPLC MS RT=1.07 min, MH+=466.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 9.48 (2H, s), 9.39 (1H, s), 8.05 (1H, d), 7.47 (1H, d), 4.59 (2H, m), 4.35 (2H, br t), 4.26 (2H, m), 4.02 (3H, s), 4.00 (2H, m), 3.67 (2H, br t), 3.52 (2H, m), 3.33 (2H, m), 3.16 (2H, m), 2.27 (2H, m).

Workup

  1. customthe precipitate was isolated by vacuum filtration

Sources & evidence

ORD record
ord-0e08be3e472640e6b1b9ce3b6ef0c15f
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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