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

HRID 10965

Reaction equation

HRID 10965 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:39](OC(=O)NC(C1C=CC(CNC([C@H]2N3C(=O)C(N)=CN=C3CC2)=O)=CC=1)=N)(C)(C)[CH3:40].CCC(=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][CH:30]([CH2:31][CH3:32])[CH2:39][CH3:40])=[CH:27][N:28]=[C:23]3[CH2:22][CH2:21]2)=[O:19])=[CH:12][CH:11]=1)=[NH:9])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 7288Ethyl ketoneHCID 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 145857228tert-butyl N-[4-[[[(6S)-4-oxo-3-(pentan-3-ylamino)-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamateYield 24%

Procedure

Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (100 mg, 0.234 mmol), 3-pentanone (33.8 mg, 0.469 mmol) and NaBH(OAc)3 (139.1 mg, 0.657 mmol) yielded 27.8 mg (24%) of intermediate 11a. MS (ESI) 497.1 (M+H+).

Sources & evidence

ORD record
ord-426cc82d056b47df9fa707ca8f83e735
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Linked notes

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