Ethyl Acetate → 1,2,3,4-Tetrahydro-3-methyl-6-[2-(methylamino)-1H-benzimidazol-1-ylmethyl]-1-(isopropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid, methyl ester

HRID 131570Notes

Reaction equation

HRID 131570 reaction equation
OC1CON(C([C:9]2[C:17]3[C:16](=[O:18])[N:15]([CH3:19])[C:14](=[O:20])[N:13]([CH:21]([CH3:23])[CH3:22])[C:12]=3[S:11][C:10]=2CC2C3C(=NC=CC=3)NC=2)=O)C1.[CH3:34][NH:35][C:36]1[NH:37][C:38]2[CH:44]=[CH:43][CH:42]=[CH:41][C:39]=2[N:40]=1.[C:45]([O:48][CH2:49]C)(=[O:47])[CH3:46]>>[CH3:19][N:15]1[C:16](=[O:18])[C:17]2[C:46]([C:45]([O:48][CH3:49])=[O:47])=[C:10]([CH2:9][N:40]3[C:39]4[CH:41]=[CH:42][CH:43]=[CH:44][C:38]=4[N:37]=[C:36]3[NH:35][CH3:34])[S:11][C:12]=2[N:13]([CH:21]([CH3:22])[CH3:23])[C:14]1=[O:20]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 676520N-Methyl-1H-benzo[d]imidazol-2-amineHCID 688045155-[[4-Hydroxyisoxazolidin-2-yl]carbonyl]-3-methyl-1-(1-methylethyl)-6-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 867606841,2,3,4-Tetrahydro-3-methyl-6-[2-(methylamino)-1H-benzimidazol-1-ylmethyl]-1-(isopropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid, methyl ester

Procedure

Prepared using the procedure described in example 13 vii) part a) from the product of example 8 part c) and 2-methylaminobenzimidazole to give the sub-title compound after trituration with ethyl acetate followed by filtration. MS(ESI) 442 [M+H]+. δ 1HDMSO 1.40-1.42 (6H,d), 2.94-2.96 (3H,d), 3.16 (3H,s), 3.85 (3H,s), 4.3 (1H, bs), 5.39 (2H,s), 6.84-6.99 (3H,m), 7.11-7.14 (1H, d), 7.20-7.22 (1H, d)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-9f36bb20396c4a0081799859323dbfc8
Source dataset
uspto-grants-2008_06
Patent number
US07384950B2

Reaction notes

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