1-Benzyl-4-methyl-pyrrolidine-3-carboxylic acid methyl ester → 6-[(3S,4S)-1-benzyl-4-methylpyrrolidin-3-yl]-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 2424804Notes

Reaction equation

HRID 2424804 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[N:5]=[C:4]([CH3:13])[C:3]=1[C:14]([NH2:16])=[O:15].CO[C:19]([C@H:21]1[C@H:25]([CH3:26])[CH2:24][N:23]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:22]1)=O>>[CH2:27]([N:23]1[CH2:24][C@@H:25]([CH3:26])[C@H:21]([C:19]2[NH:16][C:14](=[O:15])[C:3]3[C:4]([CH3:13])=[N:5][N:6]([CH:7]4[CH2:12][CH2:11][O:10][CH2:9][CH2:8]4)[C:2]=3[N:1]=2)[CH2:22]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 65589731-Benzyl-4-methyl-pyrrolidine-3-carboxylic acid methyl esterHCID 575562765-amino-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1358864816-[(3S,4S)-1-benzyl-4-methylpyrrolidin-3-yl]-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Procedure

Following the procedure for the preparation of 6-[(3,4-trans)-1-benzyl-4-methylpyrrolidin-3-yl]-1-(2-methoxyphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one but substituting 5-amino-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide and (3S,4S)-methyl-1-benzyl-4-methylpyrrolidine-3-carboxylate provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.51-7.30 (m, 5H), 4.75-4.68 (m, 1H), 4.13-4.08 (m, 2H), 3.84-3.73 (m,1H), 3.63-3.48 (m, 2H), 3.40 (m,1 H), 3.10-2.78 (m, 2H), 2.55 (s, 3H), 2.50-2.24 (m, 3H), 1.87-1.80 (m, 2H), 0.61-1.41 (m, 3H), 1.19 (d, J=6.6 Hz, 3H). MS: (M+H m/z=408.1).

Sources & evidence

ORD record
ord-aaf2b3f8d59242c2ba545ea2e0ae6263
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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