Propanal → tert-butyl N-[4-[[[(6S)-4-oxo-3-(propylamino)-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

HRID 10963

Reaction equation

HRID 10963 reaction equation
[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]([C@H:20]2[N:24]3[C:25](=[O:37])[C:26]([NH:29][CH2:30][C:31]4C=CC=C[CH:32]=4)=[CH:27][N:28]=[C:23]3[CH2:22][CH2:21]2)=[O:19])=[CH:12][CH:11]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].C(OC(=O)NC(C1C=CC(CNC([C@H]2N3C(=O)C(N)=CN=C3CC2)=O)=CC=1)=N)(C)(C)C.C(=O)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]([C@H:20]2[N:24]3[C:25](=[O:37])[C:26]([NH:29][CH2:30][CH2:31][CH3:32])=[CH:27][N:28]=[C:23]3[CH2:22][CH2:21]2)=[O:19])=[CH:12][CH:11]=1)=[NH:9])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 4

HCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 145857226tert-butyl N-[4-[[[(6S)-3-amino-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamateHCID 145857234tert-butyl N-[4-[[[(6S)-3-(benzylamino)-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

Product 1

HCID 145857210tert-butyl N-[4-[[[(6S)-4-oxo-3-(propylamino)-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamateYield 46%

Procedure

Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (100 mg, 0.234 mmol), propionaldehyde (15 mg, 0.258 mmol) and NaBH(OAc)3 (74.5 mg, 0.352 mmol) yielded 50.9 mg (46%) of intermediate 8a. MS (ESI) 469.1 (M+H+).

Sources & evidence

ORD record
ord-2b5f62a93bc94fccbdf6fca3d3a407e6
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Linked notes

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